Phenylacetic acid derivatives and fungicides containing them
Granted 15 Feb 1994 · no office action yet
Current assignee: BASF Aktiengesellschaft · originally BASF SE
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Inventors: Bernd Mueller, Gisela Lorenz, Franz Roehl, Eberhard Ammermann +1 · Examiner: John M. Ford · AU 122 · TC 1200
Life of the patent
4 dated eventsAbstract
Unsaturated phenylacetic acid derivatives of the general formula ##STR1## where U is .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3 or .dbd.CH--S--CH.sub.3 and Z.sup.1 and Z.sup.2 are hydrogen, halogen, trifluoromethyl, cyanide, NO.sub.2 or unsubstituted or substituted alkyl, alkenyl, aryl, alkynyl, alkoxy, aryloxy, arylalkoxy, acyloxy, hetaryl, --CO.sub.2 R.sup.1, --CONR.sup.2 R.sup.3, COR.sup.4 or NR.sup.5 R.sup.6, and Z.sup.1 and Z.sup.2 may also form a ring, A is meta or para and is (CH.sub.2).sub.n, CH.dbd.CH, O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, CH.sub.2 --O--CO--(CH.sub.2).sub.n, CO--O--(CH.sub.2).sub.n, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O, O--(CH.sub.2).sub.n+2 --O, CH.sub.2 O--(CH.sub.2).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n CH.sub.2 --NR.sup.7 --(CH.sub.2).sub.n, CH(CN)--O--CO--(CH.sub.2).sub.n, CH.dbd.N--(CH.sub.2).sub.n or CH.dbd.N--O--(CH.sub.2).sub.n. n is from 0 to 20, B is substituted or unsubstituted and is hydrogen, alkyl, cycloalkyl, aryl or hetaryl, R.sup.1 to R.sup.7 are hydrogen or unsubstituted or substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, hetaryl, aralkyl or cycloalkylalkyl, their acid addition products and base addition products, and fungicides and insecticides containing these compounds.
Description
73 parts›This application is continuation of application Ser. No…
This application is continuation of application Ser. No. 07/595,413, filed on Oct. 11, 1990, now abandoned.
The present invention relates to phenylacetic acid derivatives having a fungicidal and insecticidal action, fungicides containing these compounds and methods for controlling fungi.
It is known that methyl acrylate derivatives or glyoxylic ester O-methyl oxime derivatives, for example methyl 2-(2-benzoyloxyphenyl)-3-methoxyacrylate (EP-178 826), 2-benzyloxyphenylglyoxylic acid methyl ester O-methyl oxime (DE-36 23 921) or 2-phenyloxymethylenephenylglyoxylic acid methyl ester O-methyl oxime (DE-36 23 921), can be used as fungicides. However, the fungicidal action of these compounds is unsatisfactory.
We have found that novel unsaturated phenylacetic acid derivatives of the formula I ##STR2## where U is ═O, ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , ═CH--CH 3 , ═CH--CH 2 --CH 3 , ═CH--S--CH 3 ,
Z 1 and Z 2 are identical or different and are each hydrogen, halogen, trifluoromethyl, cyanide, NO 2 or the unsubstituted or substituted radicals alkyl, alkenyl, aryl, alkynyl, alkoxy, aryloxy, arylalkoxy, acyloxy, hetaryl, --CO 2 R 1 , --CONR 2 R 3 , --COR 4 or --NR 5 R 6 or Z 1 and Z 2 together form a ring which is fused with the phenyl radical of which they are substituents,
A is meta or para to the substituted methyl acetate radical and is (CH 2 ) n , O--(CH 2 ) n , O--(CH 2 ) n --CO, CH═CH--(CH 2 ) n , CH 2 O--CO--(CH 2 ) n , CO--O--(CH 2 ) n , O--CO--(CH 2 ) n , O--(CH 2 ) n --CO--O, O--(CH 2 ) n+2 --O, CH 2 --O--(CH 2 ) n , CH 2 --S--(CH 2 ) n , CH 2 --NR 7 --(CH 2 ) n , CH(CN)--O--CO--(CH 2 ) n , CH═N--(CH 2 ) n or CH═N--O--(CH 2 ) n , n is from 0 to 20,
B is hydrogen or the unsubstituted or substituted radicals alkyl, cycloalkyl, aryl or hetaryl, where the radial --A--B must not be hydrogen, and
R 1 to R 7 are identical or different and are each hydrogen or the unsubstituted or substituted radials alkyl, cycloalkyl, alkenyl, alkynyl, aryl, hetaryl, aralkyl or cycloalkylalkyl,
and their plant-tolerated acid addition products or base addition products, except for the compounds of the formulae ##STR3## have high fungitoxic and insecticidal activity and are also very well tolerated by plants.
Acids for acid addition products are, for example, mineral acids, such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid or nitric acid, or carboxylic acids, such as formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, salicylic acid, p-toluenesulfonic acid or dodecylbenzenesulfonic acid, or proton-acidic compounds generally, for example saccharin.
Bases for base addition products are, for example, potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and ammonium hydroxide.
In the preparation, the novel compounds of the formula I may be obtained as mixtures of stereoisomers (E/Z isomers, diastereomers, enantismers), which can be separated into the individual components in a conventional manner, for example by crystallization or chromatography. Both the individual isomers and mixtures thereof can be used as fungicides and form subjects of the invention.
Z 1 and Z 2 are each, for example, hydrogen, fluorine, chlorine, bromine, a straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C 1 -C 4 -alkoxy, C 2 -C 6 -alkylcarbonyloxy, phenyl, phenoxy, benzyl, benzyloxy, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzimidazolyl, quinazolyl, quinoxalyl, COOR 1 , CONR 2 R 3 , COR 4 or NR 5 R 6 , or the stated hydrocarbon, aryl or hetaryl radicals may have from 1 to 3 identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C 1 -C 8 -alkyl, C 1 -C 8 -alkylthio, C 1 -C 8 -alkylsulfinyl, cyano, hydroxyl and nitro.
Z 1 and Z 2 are each, in particular, hydrogen, fluorine, chlorine, bromine, a straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C 1 -C 4 -alkoxy, C 2 -C 6 -alkylcarbonyl, phenyl, phenoxy, benzyl or benzyloxy.
Z 1 and Z 2 are each preferably hydrogen.
A is meta or para to the substituted methyl acetate radical and is (CH 2 ) n , CH═CH--(CH 2 ) n , O--(CH 2 ) n , O--(CH 2 ) n--CO , CH 2 --O--CO--(CH 2 ) n , CO--O--(CH 2 ) n , O--CO--(CH 2 ) n , O--(CH 2 ) n--CO--O, O--(CH 2 ) n+2 --O, CH 2 --O--(CH 2 ) n , CH 2 --S--(CH 2 ) n , CH 2 --NR 7 --(CH 2 ) n , CH(CN)--O--CO--(CH 2 )═ n , CH═N--(CH 2 ) n or CH═N--O--(CH 2 ) n .
A is, in particular, (CH 2 ) n , CH═CH--(CH 2 ) n , O--(CH 2 ) n , CH 2 --O--CO--(CH 2 )═ n , CH 2 --O--(CH 2 ) n or CH 2 --S--(CH 2 ) n .
n is, for example, from 0 to 20, in particular from 0 to 10, preferably 0, 1, 2, 3 or 4.
B is, for example, an unsaturated or saturated straight-chain or branched hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C 3 -C 6 -cycloalkyl, phenyl, phenoxy, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzimidazolyl, quinazolyl or quinoxazolyl, where the stated cycloalkyl, alkyl, aryl or heteraryl radicals may have from 1 to 3 identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C 1 -C 8 -alkyl, C 1 -C 8 -alkylthio, C 1 -C 8 -alkylsulfinyl, cyano, hydroxyl and nitro.
B is preferably an unsaturated or saturated straight-chain or branched hydrocarbon radical of 1 to 6, in particular 1 to 4, carbon atoms, C 3 -C 6 -cycloalkyl, phenyl, phenoxy, pyridyl or benzoimidazolyl.
Preferred compounds are those in which the group AB is meta to the group ##STR4##
U is ═O, ═CH--OCH 3 , ═N--OCH 3 , ═N--NHCH 3 , ═CH 2 , ═CH--CH 3 , ═CH--CH 3 --CH 3 or --CH--SCH 3 , preferably ═O, ═CH--OCH 3 , ═N--OCH 3 , ═CH--CH 3 or ═CH--S--CH 3 , particularly preferably ═O, ═CH--OCH 3 , ═N--OCH 3 or ═CH--CH 3 .
›If U gives rise to syn/anti isomers, the…
If U gives rise to syn/anti isomers, the invention relates to all isomers, in particular the anti isomers.
R 1 to R 7 are each, for example, identical or different straight-chain or branched hydrocarbon radicals of 1 to 6, in particular 1 to 4, carbon atoms, cyclic hydrocarbon radicals of 3 to 6 carbon atoms, phenyl, benzyl, cyclohexylmethyl, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzoimidazolyl, quinazolyl or quinoxalyl, where the stated alkyl, cycloalkyl, aryl or hetaryl radicals may have from 1 to 3 identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, C 1 -C 8 -alkyl, C 1 -C 8 -alkylthio, C 1 -C 8 -alkylsulfinyl, cyano, hydroxyl and nitro.
The novel compounds can be prepared, for example, by the following processes:
The benzyl bromides 2 are obtained by known processes (EP 251 082) from the corresponding phenylacetic esters 1 (Scheme 1). ##STR5##
The ketoesters 5 are key intermediates and can be prepared by reacting the corresponding haloaromatics 3 with magnesium and then reacting the resulting Grignard compounds 4 with dimethyl oxalate (M. Rambaud et al., Synthesis 1988, 564), oxalic acid imidazolide methyl ester (EP 253 213) or oxalyl chloride methyl ester. The derivatives 6 can be synthesized (Scheme 2) from the ketoesters 5 by reaction with CH 3 ON + H 3 Cl - or by a Wittig reaction with (C 6 H 5 ) 3 P + --CH 2 --O--CH 3 X - or (C 6 H 5 ) 3 P + --CH 2 --CH 3 X - , where X is halogen. ##STR6##
X: Halogen
U: ═CH--OCH 3 , ═N--OCH 3 or ═CH--OCH 3
Alternatively, the ketoesters 5 are obtainable from the corresponding aldehydes 7 (Scheme 3).
The aldehydes 7 are converted into the corresponding cyanohydrins 8 by reaction with HCN. The cyanohydrins 8 are converted by reaction with HCl and methanol into the imidoester hydrochlorides 9, which are then hydrolyzed to the mandelic esters 10. These mandelic esters 10 can then be oxidized with NaOCl/tetramethylpiperidin-N-oxyl (Tempo; P. Anelli et al., JOC 52 (1987), 2559) to the ketoesters 5 (Scheme 3). ##STR7##
Either the ketoesters 5 can be brominated with NBS (N-bromosuccinimide) to give the ketoester bromides 11 (Scheme 4) or their keto functions can be reacted with P + (C 6 H 5 ) 3 --CH 2 --O--CH 3 - Cl (EP 178 826), CH 3 --O--NH 3 - Cl (EP 253 213) or H 2 N--NHCH 3 (OZ 39 772). The subsequent NBS bromination of these derivatives 12 then gives the benzyl bromides 13 (Scheme 4). ##STR8##
U: ═CH--OCH 3 , ═N--OCH 3 or ═N--NH--CH 3
Z 1 and Z 2 : as defined above
NBS: N-bromosuccinimide
The benzyl bromides 14 can be reacted with nucleophiles, eg. carboxylates (OZ 39 491), phenolates, alcoholates (EP 251 082), mercaptans (EP 226 917), amines, etc. by standard processes to give the novel compounds 15 (Scheme 5). ##STR9##
U: ═O, ═CH--OCH ═N--OCH 3 , ═N--NH--CH 3
A: CH 2 --O--(CH 2 O) n , CH 2 --S--(CH 2 ) n , CH 2 --O--CO(CH 2 ) n or CH 2 --NR 7 --(CH 2 ) n
n, B, Z 1 , Z 2 or R 7 : as defined above
Furthermore, the benzyl bromides 14 can be reacted with phosphites or phosphines to give phosphonates 16 or phosphonium salts 17, which then react with aldehydes to give the styrene derivatives 18. Hydrogenation of these styrene derivatives 18 with a diimine or with H 2 in the presence of a suitable hydrogenation catalyst, eg. Pd or Pt, in a suitable organic solvent, such as tetrahydrofuran, methanol or acetic acid, gives the alkylated aromatics 19 (cf. EP 229 974; Scheme 6). ##STR10##
U: ═O, ═CH--OCH 3 , ═N--OCH 3 or ═N--NH--CH 3
B, R 8 , R 9 and n: as defined above
The benzyl bromides 14 can also be oxidized with oxidizing agents, such as N-methylmorpholine N-oxide (OZ 50/40842, DE 2948058) or dimethyl sulfoxide (Nace et al., J. Org. Chem. 24 (1959), 1782) to give the aldehydes 20. ##STR11##
U: ═O, ═CH--OCH 3 , ═N--OCH 3 or ═N--NH--CH 3
Z 1 and Z 2 : as defined above
These aldehydes 20 react, for example in Wittig reactions similar to Scheme 6, with phosphonates or phosphonium salts to give the styrene derivatives 18.
The aldehydes 20 can also be reacted with, for example, amines or hydroxyamines or HCN to give Schiff's bases or oxime ethers 21 (Scheme 8) or cyanohydrins 22 (Scheme 9). ##STR12##
U: ═O, ═CH--OCH 3 , ═N--OCH 3 or ═N--NH--CH 3
A: CH═N--O--(CH 2 ) n or CH═N--(CH 2 ) n ,
B, Z 1 , Z 2 or n: as defined above
The hydroxyl function of the cyanohydrins 22 can be further reacted. Thus, acylated cyanohydrins 23 are obtained, for example, by reacting the compounds 22 with acyl chlorides (Scheme 9). ##STR13##
U: ═O, ═CH--OCH 3 , ═N--OCH 3 or ═N--NH--CH 3
B, n, Z 1 or Z 2 : as defined above
The benzyl bromides 11 can likewise (cf. Scheme 5) be reacted with nucleophiles, such as carboxylates, alcoholates, mercaptans, etc., the derivatives 24 being obtained. The compounds 24 can be converted into the active ingredients 25 by means of a Wittig reaction with (C 6 H 5 ) 3 P + --CH 2 --O--CH 3 Cl - (EP 178 826), C 6 H 5 P + --CH 3 X - (X=halogen), (C 6 H 5 ) 3 P + --CH 2 --CH 3 X - (X=halogen; DE 3705389) or (C 3 H 5 ) 3 P + --CH 2 --CH 2 --CH 3 X - (X=halogen) or by reaction with CH 3 --O--N + H 3 Cl - (EP 253 213) or H 2 N--NHCH 3 (Scheme 10) . ##STR14##
A: CH 2 --O--CO, CH 2 --O--(CH 2 ) n , CH 2 --S--(CH 2 ) n or CH 2 --NR 7 (CH 2 ) n
U: ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , ═CH--CH 3 or ═CH--CH 2 --CH 3
B, n, Z 1 , Z 2 or R as defined above.
Active ingredients of the structure 28 are obtained from the corresponding hydroxyphenylacetic esters 26, for example by alkylation of the compounds 26 to give the phenyl ethers 27 and subsequent formulation/methylation of 27 (EP 251 082) to give the active ingredients 28 (Scheme 11). ##STR15##
A: O--(CH 2 ) n , O--(CH 2 ) n+1 --CO or O--(CH 2 ) n+2 --O
B, n, Z 1 or Z 2 : as defined above
Alternatively, the hydroxyl function of the compounds 26 can be protected by a suitable protective group, eg. tetrahydropyranyl or benzyl.
Formylation/methylation (EP 251 082) of these protected phenols 29 then gives the methyl α-phenyl-β-methoxyacrylates 30, from which the phenols 31 can be liberated by treatment with hydrochloric acid in methanol or by catalytic hydrogenation (Scheme 12). ##STR16##
›SG: Protective group, eg. benzyl or tetrahydropyranyl The…
SG: Protective group, eg. benzyl or tetrahydropyranyl
The phenols 31 can then be reacted with electrophiles under standard conditions, the active ingredients 32 being obtained (Scheme 13). ##STR17##
A: O--(CH 2 ) n , O--(CH 2 ) n --CO, O--CO--(CH 2 ) n , O--(CH 2 ) n --CO--O or O--(CH 2 ) n+2 --O
B, n, Z 1 or Z 2 : as defined above
Other useful starting materials for the preparation of the novel compounds 41 are the hydroxybenzaldehydes 33.
The hydroxybenzaldehydes 33 can be reacted with benzyl bromide under base catalysis. The benzylated derivatives 34 thus obtained are converted into the corresponding cyanohydrins 35 by reaction with HCN.
These can be reacted with methanol and hydrochloric acid to give the imidoester hydrochlorides 36, which can be hydrolyzed to the mandelic esters 37.
The compounds 37 are oxidized with tetramethylpiperidine-N-oxyl (Tempo: P. Anelli et al., JOC 52 (1987), 2559)/NaOCl to give the ketoesters 38. These can be subjected to hydrogenolysis to give the phenols 39, which in turn react with methoxyamine hydrochloride or H 2 N--NHCH 3 to give the phenolic building blocks 40. These can be etherified or esterified, the novel active ingredients 41 being obtained (Scheme 14). Alternatively, the ketoesters 39 are etherified or esterified to the compounds 42. The derivatives 42 are then converted into the active ingredients 41 by reaction with CH 3 --O--NH 3 Cl or H 2 N--NHCH 3 (Scheme 14). ##STR18##
A: O--(CH 2 ) n , O--(CH 2 ) n --CO, O--CO--(CH 2 ) n , O--(CH 2 ) n --CO--O or O--(CH 2 ) n+2 --O
U: ═N--OCH 3 or ═N--NH--CH 3
B, n, Z 1 or Z 2 : as defined above
The ketoesters 38 can on the other hand also be subjected to Wittig reactions under base catalysis with (C 6 H 5 ) 3 P + --CH 2 --O--CH 3 X - , (C 6 H 5 ) 3 P + --CH 3 X - , (C 6 H 5 ) 3 P + --CH 2 --CH 3 X - or (C 6 H 5 ) 3 P + --CH 2 --CH 2 --CH 3 X - to give the benzyl ethers 43 (X=halogen).
The benzyl group can then be eliminated from these by hydrogenolysis or a free radical reaction, the phenols 44 being obtained. These can be etherified or esterified to the active ingredients 45 in reactions similar to Schemes 13 and 14 (Scheme 15). ##STR19##
U: ═CH--OCH 3 , ═CH 2 , ═CH--CH 3 or ═CH--CH 2 --CH 3
A: O--(CH 2 ) n , O--(CH 2 ) n --CO, O--CO--(CH 2 ) n , O--(CH 2 ) n --CO--O or O--(CH 2 ) n+2 --O
B, n, Z 1 and Z 2 : as defined above
Alternatively, the active ingredients 48 can be prepared by a method similar to Schemes 14 and 15 by introducing the side chain into the hydroxybenzaldehydes 33 themselves.
The benzaldehydes 46 thus obtained are then converted by the method described in Scheme 14 into the phenylketoacetates 47, which give the active ingredients 48 by a Wittig reaction with (C 6 H 5 ) 3 P + --CH 2 --O--CH 3 X - , (C 6 H 5 ) 3 P + --CH 3 X - , (C 6 H 5 ) 3 P + --CH 2 --CH 3 X - or (C 6 H 5 ) 3 P + --CH 2 --CH 2 --CH 3 X + (X=halogen) or by reaction with CH 3 --O--N + H 3 Cl - or H 2 N--NHCH 3 (Scheme 16). ##STR20##
U: ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , ═CH--CH 3 or ═CH--CH 2 --CH 3
A: O--(CH 2 ) n , O--(CH 2 ) n --CO, O--CO--(CH 2 ) n , O--(CH 2 ) n --CO--O or O--(CH 2 ) n+2 --O
B, n, Z 1 and Z 2 : as defined above
The benzyl bromides 11 described in Scheme 4 can also be used for the synthesis of further key intermediates (Scheme 17). For example, the benzyl bromides 11 can be reacted with Na acetate or K acetate in highly solvating solvents, such as dimethylformamide or N-methylpyrrolidone, to give the acetates 49. The latter react under base catalysis with (C 6 H 5 ) 3 P + --CH 2 --O--CH 3 X - , (C 6 H 5 ) 3 P + --CH 3 X - , (C 6 H 5 ) 3 P + --CH 2 --CH 3 X - or (C 6 H 5 ) 3 P + --CH 2 --CH 2 --CH 3 X - (X=halogen) in Wittig reactions or with CH 3 ON + H 3 Cl - or H 2 N--NHCH 3 , the derivatives 50 being formed.
The benzyl alcohols 51 and 52 are obtainable from the derivatives 49 and 50 by alkaline ester hydrolyis with aqueous alkali in the presence of a solubilizer, such as acetonitrile, dioxane or tetrahydrofuran. ##STR21##
U: ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , ═CH--CH 3 or ═CH--CH 2 --CH 3
Z 1 and Z 2 : as defined above
The benzyl bromides 13, likewise obtained according to Scheme 4, can be converted into the acetates 53 (Scheme 18) similarly to Scheme 17. ##STR22##
U: ═CH--OCH 3 , ═N--OCH 3 or ═N--NH--CH 3
Z 1 and Z 2 : as defined above
The benzyl alcohols 54 can be converted into the benzaldehydes 55 by oxidation with suitable oxidation agents, such as dimethyl sulfoxide or pyridinium chlorochromate, into the benzoic acid 56 by oxidation with, for example, chromium(VI) oxide in acetone/sulfuric acid and into the bromides 57 or chlorides 58 by reaction with suitable hydrogenating agents, eg. PBr 3 or HBr or PCl 5 , SOCl 2 or PCl 3 (Scheme 19). ##STR23##
U: ═O, ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , ═CH--CH 3 or ═CH--CH 2 --CH 3
Z 1 and Z 2 : as defined above
The active ingredients 59 are obtainable (Scheme 19) from the benzaldehydes 55 similarly to the reactions described in Schemes 6, 8 and 9. ##STR24##
A: HC═CH, CH 2 --CH 2 , CH(CN)--OH, CH(CN)--O--CO--(CH 2 ) n , CH═N--(CH 2 ) n or CH═N--O--(CH 2 ) n
U: ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , ═CH--CH 3 or ═CH--CH 2 --CH 3
B, Z 1 and Z 2 : as defined above
The benzoic acids 56 can be esterified under standard conditions, the benzoic esters 60 being obtained (Scheme 21). ##STR25##
U: ═O, ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , ═CH--CH 3 or ═CH--CH 2 --CH 3
Z 1 and Z 2 : as defined above
The benzyl bromides 57 or chlorides 58 can be converted into stilbene or dihydrostilbenes 61 in reactions similar to Scheme 6, via their phosphonium salts or phosphonates (Scheme 22). ##STR26##
U: ═CH--OCH 3 , ═N--OCH 3 , ═N--NH--CH 3 , ═CH 2 , --CH--CH 3 or --CH--CH 2 --CH 3
A: HC═CH, H 2 C--CH 2
B, Z 1 and Z 2 : as defined above
The thioenolethers 63 can be prepared from the corresponding oxo analogs 64 by methods known from the literature (EP 178 826) (Scheme 23). ##STR27##
A, B, Z 1 and Z 2 : as defined above
The Examples which follow illustrate the preparation of the novel compounds.
›Examples23
›EXAMPLE 1
a) Methyl m-methylmandelate
A mixture of 65 g (1 mol) of KCN and 53.5 g (1 mol) of NH 4 Cl in 300 ml of water and 60 g (0.5 mol) of m-tolylaldehyde in 500 Ml Of ether is stirred overnight at room temperature (20° C.). Thereafter, the organic phase is separated off, extracted twice with water, dried and evaporated down.
67.6 g of the cyanohydrin are obtained as a reddish brown oil.
67.6 g (about 0.5 mol) of the crude cyanohydrin product are dissolved in 600 ml of ether and the solution is cooled to 0° C.
32 g (1 mol) of methanol and 136 ml (0.6 mol) of a 4.4 M solution of hydrochloric acid in ether are added in succession and the mixture is stirred overnight at 10°-15° C. and for a further two days at room temperature. The imidoester hydrochloride which is crystallized out is filtered off under suction, washed with ether, transferred to a flask and hydrolyzed by boiling for 30 minutes with water.
The aqueous phase is cooled to room temperature and extracted twice with ether. The ether phase is filtered over a short silica gel column, dried over MgSO 4 and evaporated down. 40 g (0.22 mol; 44% based on m-tolylaldehyde) of methyl m-methylmandelate are obtained as the residue in the form of a yellow oil.
1 H-NMR (CDCl 3 ): δ: 2.3 (s, 3H); 3.7 (s, 3H); 4.1 (s, broad, 1H); 5.1 (s, 1H); 7.1 (m, 4H).
b) Methyl m-methylphenylglyoxylate (Table 1, Number 1, abbreviation: 1/1)
170 ml of 12.5% strength NaOCl solution are added dropwise at 20° C. to a stirred mixture of 40 g (0.22 mol) of methyl m-methylmandelate and 1.5 g (9.6 mmol) of tetramethylpiperidine-N-oxyl in 200 ml of CH 2 Cl 2 and 1.4 g (13 mmol) KBr, 3.5 g (25 mmol) of NaH 2 PO 4 .H 2 O and 4.3 g (25 mmol) of Na 2 HPO 4 .2 H 2 O in 200 ml of water.
Stirring is carried out for 3 hours at room temperature, after which the organic phase is separated off, washed with NAHCO 3 solution and water and evaporated down.
The residue obtained comprises 37.5 g (0.21 mol, 96%) of methyl m-methylphenylglyoxylate as a yellow oil.
1 H-NMR (CDCl 3 ): δ: 2.4 (s, 3H); 4.0 (s, 3H); 7.4 (m, 2H); 7.8 (m, 2H).
›EXAMPLE 2
a) Methyl m-bromomethylenephenylglyoxylate (Table 1, Number 2, abbreviation 1/2)
18 g (0.1 mol) of methyl m-methylphenylglyoxylate, 20 g (0.11 mol) of N-bromosuccinimide and 0.1 g (0.6 mmol) of azoisobutyronitrile in 200 ml of CCl 4 are exposed for 4 hours to a 300 watt UV lamp, the solution heating up to the reflux temperature.
The precipitated succinimide is then filtered off under suction. The organic phase is washed with water, dried with MgSO 4 and filtered under suction over a little silica gel, and the filtrate is evaporated down. 28.6 g of a reddish brown oil are obtained, which is shown by NMR analysis to contain 65% of the desired compound methyl m-bromomethylenephenylglyoxylate (70%, based on methyl m-methylphenylglyoxylate), about 20% of the corresponding dibromide and about 15% of starting material.
1 H-NMR (CDCl 3 ): δ: 4.0 (s, 3H); 4.55 (s, 2H); 7.3-8.2 (m, 4H).
b) Methyl m- (o-methylphenoxymethylene) -phenylglyoxylate (Table 2, Number 490, abbreviation 2/490)
0.6 g (24 mmol) of NaH is added a little at a time to a solution of 2.2 g (20.4 mmol) of o-cresol in 50 ml of dimethylformamide at room temperature, vigorous evolution of gas occurring. 5.1 g of the crude methyl m-bromomethylenephenylglyoxylate (Example 1c; contains 13 mmol of the benzyl bromide) are then added. The reaction mixture warms up to about 40° C.
Stirring is carried out for 4 hours at room temperature, the reaction mixture is diluted with water and the aqueous phase is extracted several times with ether. The combined ether phases are washed several times with Na 2 CO 3 solution and water, dried over MgSO 4 and evaporated down.
The residue is purified by column chromatography, after which 3.8 g of the desired product, contaminated with o-cresol, are obtained.
Bulb tube distillation (0. 1 mbar; 175°-225° C.) gives 2.4 g (65%) of methyl m-(o-methylphenoxymethylene)phenylglyoxylate as a yellow oil.
1 H-NMR (CDCl 3 ): δ: 4.0 (s, 3H); 5.1 (s, 2H); 6.7-7.2 (m, 4H); 7.5 (t, J=9Hz, 1H); 7.7 (d, J=9Hz, 1H); 8.0 (d, J=9Hz, 1H); 8.1 (d, J=9Hz, 1H).
›EXAMPLE 3
Methyl 2-[m-(o-methylphenoxymethylene)-phenyl]-crotonate (Table 6, Number 65, abbreviation 6/65)
5.8 ml of a 15% strength solution of butyllithium in hexane are added to 4.2 g (10 mmol) of ethyltriphenylphosphonium iodide in 20 ml of tetrahydrofuran at 0° C. while stirring.
After 30 minutes at room temperature, the mixture is cooled to -780° C., a pale yellow solid being precipitated, and a solution of 2.4 g (8 mmol) of methyl m-(o-methylphenoxymethylene)-phenylglyoxylate in tetrahydrofuran is added. The color of the reaction mixture changes from orange to yellow.
The reaction mixture is stirred for 2 hours at room temperature, after which it is poured onto water, the phases are separated and the aqueous phase is extracted several times with ether.
The ether phase is dried over MgSO 4 and filtered under suction over a short silica gel column, and the filtrate is evaporated down.
The remaining oil is chromatographed once with 5:1 cyclohexane/ethyl acetate and once with 4:1 cyclohexane/methylene chloride. 0.8 g (34%) of methyl 2-[m-(o-methylphenoxymethylene)-phenyl]-crotonate is obtained as a yellow oil.
1 H-NMR (CDCl 3 ): δ: 1.7 (d, 8Hz, 3H); 2.3 (s, 3H); 3.7 (s, 3H); 5.1 (s, 2H); 6.8-7.5 (m, 9H).
›EXAMPLE 4
m-Methylphenylglyoxylic acid methyl ester O-methyl oxime (Table 1, Number 37, abbreviation 1/37)
15 g (84 mmol) of methyl m-methylphenylglyoxylate and 8.3 g (100 mmol) of O-methylhydroxylamine hydrochloride in 150 ml of methanol are refluxed for 5 hours. Thereafter, the solvent is evaporated off and the residue is filtered with ether over silica gel.
Evaporating off the ether gives 16.2 g (93%) of m-methylphenylglyoxylic acid methyl ester O-methyl oxime as an oily cis/trans mixture (nonpolar isomer:polar isomer=25:1).
1 H-NMR (CDCl 3 ): δ (nonpolar isomer): 2.35 (s, 3H); 3.93 (s, 3H); 4.0 (s, 3H); 7.1-7.5 (m, 4H); δ (polar isomer) 2.38 (s, 3H) ; 3.87 (s, 3H) ; 4.05 (s, 3H); 7.1-7.5 (m, 4H).
›EXAMPLE 5
m-Bromomethylenephenylglyoxylic acid methyl ester O-methyl oxime (Table 1, Number 38, abbreviation 1/38)
15 g (72.4 mmol) of m-methylphenylglyoxylic acid methyl ester O-methyl oxime, 13.5 g (75.8 mmol) of N-bromosuccinimide and 0.1 g (0.6 mmol) of azobisisobutyrodinitrile in 150 ml of CH 2 Cl 2 are exposed for 4 hours to a 300 watt UV lamp, the reaction mixture being refluxed. Thereafter, the organic phase is extracted with water, dried over MgSO 4 and evaporated down.
Purification by column chromatography gives 10.7 g of the nonpolar isomer and 6.1 g of the polar isomer, each of which contains about 5% of the corresponding dibromide and about 10% of the starting material.
1 H-NMR (CDCl 3 ): δ (nonpolar isomer): 3.95 (s, 3H); 4.05 (s, 3H); 4.5 (s, 2H); 7.2-7.5 (m, 3H); 7.6 (s, 1H); δ (polar isomer): 3.90 (s, 3H); 4.10 (s, 3H); 4.5 (s, 2H); 7.2-7.5 (m, 4H).
›EXAMPLE 6
m-(6-methyl-2-oxymethylenepyridyl)-phenylglyoxylic acid methyl ester O-methyl oxime (Table 20, Number 2, abbreviation 20/2)
0.18 g (6.3 mmol) of NaH is added to 0.76 g (7 mmol) of 2-hydroxy-6-methylpyridine in 20 ml of dimethylformamide. Stirring is carried out for 30 minutes at room temperature, after which evolution of gas has ceased.
2 g of m-bromomethylenephenylglyoxylic acid methyl ester O-methyl oxime (nonpolar isomer, containing 1.7 g (6 mmol) of the substituted benzyl bromide) are then added and the mixture is stirred overnight at room temperature. Thereafter, the reaction mixture is diluted with water and the aqueous phase is extracted three times with ether. The combined ether phases are extracted with water, dried over MgSO 4 and evaporated down.
The oily residue is chromatographed with 1:1 cyclohexane/methylene chloride.
0.5 g (27%) of m-(6-methyl-2-oxymethylenepyridyl)-phenylglyoxylic acid methyl ester O-methyl oxime is obtained as a yellow oil.
1 H-NMR (CDCl 3 ): δ: 2.45 (s, 3H); 3.95 (s, 3H); 4.05 (s, 3H); 5.4 (s, 2H); 6.6 (d, J=8Hz, 1H); 6.75 (d, J=8Hz, 1H); 7.3-7.6 (m, 4H); 7.7 (s, 1H).
›EXAMPLE 7
2-(N-methyl-N-phenyl-m-aminomethylphenyl)-3-methoxyacrylate (Table 2, Number 88)
2.9 g (10 mmol) of methyl 2-(m-bromomethylphenyl)-3-methoxyacrylate (prepared similarly to EP 226 917) and 1.1 g (10 mmol) of N-methylaniline in 30 ml of CH 2 Cl 2 are stirred for 1 hour at room temperature and for 5 hours while refluxing. Thereafter, the organic phase is extracted with NaHCO 3 solution and water, dried over MgSO 4 and evaporated down.
Chromatography with 10:1 cyclohexane/ethyl acetate gives 2.5 g (80%) of the title compound as a pale yellow oil.
1 H-NMR (CDCl 3 ): δ: 3.0 (s, 3H); 3.65 (s, 3H); 3.75 (s, 3H); 4.5 (s, 3H); 6.6-6.8 (m, 3H); 7.0-7.4 (m, 6H); 7.5 (s, 1H).
›EXAMPLE 8
a) Methyl 2-(m-formylphenyl)-3-methoxyacrylate (Table 1, Number 22)
5.7 g (20 mmol) of methyl 2-(m-bromomethylphenyl)-3-methoxyacrylate and 6.7 g (50 mmol) of N-methylmorpholine N-oxide monohydrate in 100 ml of CCl 4 are refluxed for 7 hours. The reaction mixture is cooled and is extracted once with water, once with 2 N HCl and again with water. The organic phase is dried over MgSO 4 and evaporated down.
The oily residue is chromatographed with 4:1 cyclohexane/ethyl acetate, after which 3.0 g (13.6 mmol, 68%) of methyl 2-(m-formylphenyl)-3-methoxyacrylate are obtained as a colorless oil.
1 H-NMR (CDCl 3 ): δ: 3.75 (s, 3H); 3.85 (s, 3H); 7.5 (t, J=8Hz, 1H); 7.65 (m, 2H); 7.8 (d, broad, J=8Hz, 1H); 7.9 (s, broad, 1H); 10 (s, 1H).
b) Methyl 2-[m-(α-phenylcarboxy)-cyanomethylphenyl]-3-methoxyacrylate ((Table 2, Number 95)
A mixture of 2.9 g (13 mmol) of methyl 2-(m-formylphenyl)-3-methoxyacrylate in 20 ml of ether and 1.7 g (26 mmol) of KCN and 1.5 g (26 mmol) of NH 4 Cl in 7.5 ml of water is stirred at room temperature overnight, after which only a small amount of starting material is detectable by thin layer chromatography.
Thereafter, the reaction mixture is diluted with a little water, and the aqueous phase is separated off and is extracted twice with ether. The combined organic phases are dried over MgSO 4 and evaporated down.
The remaining oil is subjected to coarse chromatographic purification to give 2.4 g of a colorless oil, which is directly reacted further.
1.4 g (10 mmol) of benzoyl chloride are added dropwise to 2.4 g (about 10 mmol) of the crude cyanohydrin product, 1.1 g (11 mmol) of triethylamine and 0.1 g of p-N-dimethylaminopyridine in 20 ml of CH 2 Cl 2 while cooling slightly, a white solid being precipitated.
After 1 hour at room temperature, the reaction mixture is washed once with water, twice with Na bisulfite solution and again with water, dried over MgSO 4 and evaporated down. The remaining oil is chromatographed once with 8:1 cyclohexane/ethyl acetate and once with 0.1% methanol in methylene chloride, after which 2.1 g (6 mmol), 46% based on methyl 2-(m-formylphenyl)-3-methoxyacrylate) of the title compound are obtained as a colorless oil.
1 H-NMR (CDCl 2 ): δ: 3.75 (s, 3H); 3.85 (s, 3H); 6.7 (s, 1H), 7.4-7.7 (m, 9H); 8.1 (d, J=8Hz, 1H).
›EXAMPLE 9
2-(p-Benzyloxyphenyl)-3-methoxyacrylate (Table 1, Number 33)
90 g (0.54 mol) of methyl 4-hydroxyphenylacetate, 60 g (0.71 mol) of dihydropyran and 0.1 g of p-toluenesulfonic acid are combined. The temperature of the mixture initially decreases to 5°-10° C. but increases again in the course of the reaction and is kept at 30°-35° C. by cooling in a water bath. After 1 hour, the excess dihydropyran is stripped off under reduced pressure from a water pump.
The crude tetrahydropyranyl ether product is dissolved in 220 ml of methyl formate, and 44 g (0.78 mol) of NaOCH 3 are added while cooling to about 10° C.
After 2 hours at room temperature, the reaction mixture is diluted with CH 2 Cl 2 and water and the aqueous phase is acidified to pH 4.5 with dilute hydrochloric acid and is extracted several times with CH 2 Cl 2 . The combined organic phases are dried over MgSO 4 and evaporated down.
The oily crude product obtained as the residue is dissolved in 700 ml of . . . , 90 g (0.65 mol) of K 2 CO 3 and 74 g (0.59 mol) of dimethyl sulfate are added and the mixture is stirred overnight at room temperature.
The reaction mixture is then evaporated down in a rotary evaporator and the residue is diluted with water. The aqueous phase is extracted several times with ether. The combined ether phases are dried over MgSO 4 and evaporated down.
The crude methyl 2-(p-tetrahydropyranyloxyphenyl)-3-methoxyacrylate thus obtained is dissolved in 700 ml of methanol, and 0.5 ml of concentrated hydrochloric acid and 5 ml of water are added. After 2 hours at room temperature, 2 g of NaHCO 3 are added and the reaction mixture is evaporated down in a rotary evaporator.
The oily residue is taken up in CH 2 Cl 2 , and the solution is dried over MgSO 4 and evaporated down. The residue is partially crystalline and is stirred with methyl tert-butyl ether. The solid is filtered off under suction, the mother liquor is evaporated down and the residue is chromatographed.
The title compound is obtained as a white solid (mp.=107°-109° C.) in a total yield of 66 g (0.32 mol; 59%, based on methyl p-hydroxyphenyl acetate).
1 H-NMR (CDCl 3 ): δ: 3.75 (s, 3H); 3.8 (s, 3H); 6.75 (d, J=8Hz, 2H); 7.15 (d, J=8Hz, 2H); 7.5 (s, 1H).
›EXAMPLE 10
2-(p-Benzyloxyphenyl)-3-methoxyacrylate (Table 3, Number 14)
1. 8 g (10. 5 mmol) of benzyl bromide are added, at -20° C., to 2.1 g (10 mmol) of methyl 2-(p-hydroxyphenyl)-3-methoxyacrylate and 0.56 g (10 mmol) of KOH powder in 20 ml of dimethylformamide. Stirring is then carried out for 3 hours at room temperature. Thereafter, the reaction mixture is diluted with water and the aqueous phase is extracted three times with ether.
The combined ether phases are extracted with water, dried over MgSO 4 and evaporated down. Chromatographic purification of the oily residue gives 2.4 g (8.1 mmol, 80%) of the title compound as a colorless solid (mp.=77°-79° C.).
1 H-NMR (CDCl 3 ) : δ: 3.75 (s, 3H); 3.85 (s, 3H); 5.1 (s, 2H); 6.95 (d, J=11Hz, 2H); 7.2-7.5 (m, 7H); 7.55 (s, 1H).
›EXAMPLE 11
Methyl 2-m-(phenylcarbonylmethyleneoxyphenyl)-3-methoxyacrylate (Table 2, Number 19)
0.3 g (12 mmol) of sodium hydride is added a little at a time to 2.1 g (10 mmol) of methyl 2-m-hydroxyphenyl-3-methoxyacrylate (Table 1, Number 24; prepared similarly to Example 5a) in 20 ml of dimethylformamide.
After the end of the addition, the reaction mixture is stirred for 30 minutes at room temperature, after which 3.3 g (1.6 mmol) of a-bromoacetophenone are added.
Stirring is continued overnight at room temperature, after which the reaction mixture is diluted with water and the aqueous phase is extracted three times with ether. The ether phase is extracted with water, dried over magnesium sulfate and evaporated down.
The remaining oil is chromatographed, 1.1 g (3.4 mmol, 34%) of the title compound being obtained as a white solid (mp. 103°-105° C.).
1 H-NMR (CDCl 3 ): δ: 3.35 (s, 2H); 3.65 (s, 3H); 3.8 (s, 3H); 5.55 (s, 2H); 6.8 (m, 3H); 7.2 (t, J=8Hz, 1H); 7.5-7.8 (m, 4H); 8.05 (d, J=8Hz, 2H).
›EXAMPLE 12
a) Methyl m-benzyloxymandelate
61 g (0.5 mol) of m-hydroxybenzaldehyde, 86 g (0.5 mol) of benzyl bromide and 70 g (0.5 mol) of K 2 CO 3 in 500 ml of ethanol are refluxed for 3 hours.
The solid is then filtered off and the ethanol is evaporated off in a rotary evaporator. Thereafter, the residue is taken up in CH 2 Cl 2 and the organic phase is extracted with 1 NAOH and twice with water. The solution is dried over MgSO 4 and the solvent is evaporated under reduced pressure.
The residue obtained comprises 102.5 g of m-benzyloxybenzaldehyde as a reddish brown oil.
A mixture of 102.5 g of the above crude benzyl ether in 400 ml of ether and 65 g (1 mol) of KCN and 53.5 g (1 mol) of NH 4 Cl in 300 ml of water is stirred overnight at room temperature. Thereafter, the organic phase is separated off, extracted twice with NaCl solution, dried over MgSO 4 and evaporated down. The residue obtained comprises 113 g of m-benzyloxymandelonitrile as a brown oil which is directly reacted further.
140 ml of 4.4 molar hydrochloric acid solution (0.62 mol) in ether are added, at 0°-50° C., to 113 g of the crude mandelonitrile product and 32 g (1 mol) of methanol in 500 ml of ether. Stirring is carried out overnight at 5°-15° C.; the corresponding imidoester hydrochloride is precipitated and is filtered off under suction and washed with ether (yield: 107 g). The solid is transferred to a round-bottomed flask and boiled for 30 minutes with 500 ml of water. Thereafter, the reaction mixture is cooled to room temperature and the aqueous phase is extracted with ether.
The combined ether phases are filtered with suction through silica gel, dried over MgSO 4 and evaporated down.
86 g (0.32 mol; 63%, based on m-hydroxybenzaldehyde) of methyl m-benzyloxymandelate are obtained as a residue.
1 H-NMR (CDCl 3 ): δ: 3.5 (s, broad, 1H); 3.7 (s, 3H); 5.05 (s, 2H); 5.15 (s, 1H); 6.8-7.1 (m, 3H); 7.2-7.5 (m, 6H).
b) Methyl m-benzyloxyphenylglyoxylate
245 ml of 12.5% strength NaOCl solution are added dropwise to a stirred mixture of 86 g (0.32 mol) of methyl m-benzyloxymandelate and 2 g (13 mmol) of tetramethylpiperidine-1-oxyl in 250 ml of CH 2 Cl 2 and 1.95 g (16 mmol) of KBr, 4.9 g (28 mmol) of Na 2 HPO 4 .2H 2 O and 6.1 g (44 mmol) of NaH 2 PO 4 .H 2 O in 250 ml of water, while cooling with a water bath.
Stirring is carried out for 3 hours at room temperature, the aqueous phase is separated off and the organic phase is extracted with NaHCO 3 solution and with water. The organic phase is dried over MgSO 4 and evaporated down. 78 g (0.29 mol, 90%) of methyl m-benzyloxyphenylglyoxylate are obtained as a residue.
1 H-NMR (CDCl 3 ): δ: 3.95 (s, 3H); 5.1 (s, 2H); 7.1-7.7 (m, 9H).
›EXAMPLE 13
m-Benzyloxyphenylglyoxylic acid methyl ester O-methyl oxime (Table 2, Number 119)
4 g (15 mmol) of methyl m-benzyloxyphenylglyoxylate and 1.4 g (17 mmol) of O-methylhydroxylamine hydrochloride in 25 ml of ethanol are refluxed for 3 hours. The reaction mixture is then evaporated down. The residue is taken up in ether and the insoluble constituents are filtered off.
The solvent is evaporated off and the remaining residue is purified by column chromatography.
3.1 g (10.4 mmol, 69%) of the nonpolar isomer (colorless crystals, mp.=62°-63° C.) and 0.9 g (3 mmol, 20%) of the polar isomers (colorless crystals, mp.=63°-64° C.) of the title compound are obtained.
1 H-NMR (CDCl 3 ) of the nonpolar isomer: δ: 3.9 (s, 3H); 4.0 (s, 3H); 5.05 (s, 2H); 6.95-7.5 (m, 9H).
1 H-NMR (CDCl 3 ) of the polar isomer: δ: 3.85 (s, 3H); 4.05 (s, 3H); 5.05 (s, 2H); 7.0 (m, 3H); 7.2-7.5 (m, 6H).
›EXAMPLE 14
a) m-Hydroxyphenylglyoxylic acid methyl ester O-methyl oxime (Table 1, Number 42)
65 g (0.24 mol) of methyl m-benzyloxyglyoxylate and 6 g of 10% strength Pd/C in 500 ml of methanol are stirred at 60° C. under hydrogen (1 bar).
After a reaction time of 8 hours in each case, the hydrogenation catalyst is filtered off and the same amount of fresh catalyst is added.
After a total reaction time of 32 hours, the reaction is complete. The catalyst is filtered off and the reaction mixture is evaporated down. The residue obtained comprises 42 g of methyl m-hydroxyphenylglyoxylate as an oily crude product.
21 g of the above crude product and 10 g (0.12 mol) of O-methylhydroxylamine hydrochloride in 200 ml of methanol are refluxed for 2 hours.
Thereafter, the solvent is distilled off, the residue is taken up in ether and the undissolved constituents are filtered off. The ether is evaporated off and the residue thus obtained is purified by column chromatography. 8.7 g (42 mmol; 35%, based on methyl mbenzyloxyphenylglyoxylate) of the nonpolar isomer (pale yellow oil) and 4.2 g (20 mmol; 17%, based on methyl mbenzyloxyphenylglyoxylate) of the polar isomer of the title compound are obtained.
1 H-NMR (CDCl 3 ) of the nonpolar isomer: δ: 3.9 (s, 3H); 4.0 (s, 3H); 5.7 (s, broad, 1H); 6.9 (d, J=8Hz, 1H); 7.1 (m, 2H); 7.2 (t, J=8Hz, 1H).
1 H-NMR (CDCl 3 ) of the polar isomer: δ: 3.85 (s, 3H); 4.05 (s, 3H); 6.2 (s, broad, 1H); 6.8-7.0 (m, 3H); 7.2 (t, J=8Hz, 1H).
›EXAMPLE 15
m-(o-Fluorobenzyloxy)-phenylglyoxylic acid methyl ester O-methyl oxime (Table 5, Number 1)
0.3 g (12.5 mmol) of sodium hydride is added a little at a time to 2.1 g (10 mmol) of m-hydroxyphenylglyoxylic acid methyl ester O-methyl oxime (nonpolar isomer:polar isomer=2:1) in 20 ml of dimethylformamide. Stirring is carried out for 30 minutes at room temperature, 1.9 g (10 mmol) of 2-fluorobenzyl bromide are added and stirring is continued overnight at room temperature.
The reaction mixture is then diluted with water and extracted with ether. The combined ether phases are extracted with water, dried over MgSO 4 and evaporated down. Purification of the residue by column chromatography gives 1.7 g (5.4 mmol, 54%) of the nonpolar isomer (pale yellow oil) and 0.5 g (1.6 mmol, 16%) of the polar isomer (colorless solid, mp.=77°-79° C.) of the title compound.
1 H-NMR (CDCl 3 ) of the nonpolar isomer: δ: 3.9 (s, 3H); 5.1 (s, 2H); 6.9-7.6 (m, 8H).
1 H-NMR (CDCl 3 ) of the polar isomer: δ: 3.85 (s, 3H), 4.05 (s, 3H); 5.1 (s, 2H); 6.9-7.6 (m, 8H).
›EXAMPLE 16
Methyl 2-(p-acetoxyphenyl)-3-methoxyacrylate (Table 3, Number 22)
3 g (10.5 mmol) of methyl 2-(p-bromomethylphenyl)-3-methoxyacrylate (prepared similarly to EP 226 917), 1.1 g (11.2 mmol) of potassium acetate and 50 mg of potassium iodide in 70 ml of N-methylpyrrolidone are stirred for 3 hours at 70°-80° C. The reaction mixture is diluted with water and extracted three times with ether. The combined ether phases are washed with water, dried over MgSO 4 and evaporated down. Purification of the residue by column chromatography gives 2.3 g (8.7 mmol, 83%) of the title compound as colorless crystals (mp.= 69°-70° C.).
1 H-NMR (CDCl 3 ): δ: 2.1 (s, 3H); 3.75 (s, 3H); 3.85 (s, 3H); 5.1 (s, 2H); 7.35 (s, 4H); 7.6 (s, 1H).
›EXAMPLE 17
Methyl 2- (p-hydroxymethylphenyl) -3-methoxyacrylate (Table 1, Number 36)
12 g (45 mmol) of methyl 2-(p-acetoxyphenyl)-3-methoxyacrylate in 200 ml of dioxane and 1.9 g (47 mmol) of NAOH in 100 ml of water are stirred for 24 hours at room temperature. A further 1.8 g of NAOH are added, stirring is carried out for 30 minutes and the reaction mixture is evaporated down under reduced pressure.
The residue is taken up with dilute hydrochloric acid and the aqueous phase is extracted three times with ether. The ether phase is filtered under suction over Al 2 O 3 and the solvent is evaporated off. The residue obtained comprises 4.2 g (19 mmol, 40%) of the title compound as a colorless oil.
1 H-NMR (CDCl 3 ): δ: 2.4 (s, broad, 1H); 3.75 (s, 3H); 3.85 (s, 3H); 4.65 (s, 2H); 7.3 (s,-4H); 7.55 (s, 1H)
›EXAMPLE 18
Methyl 2-(p-carboxyphenyl)-3-methoxyacrylate (Table 1, Number 32)
5 ml of Jones reagent (L. Chinn, Selection of Oxidants in Synthesis, Marcel Dekker, New York 1971, page 42) are added dropwise, at from -10° to -20° C., to 2.2 g (10 mmol) of methyl 2-(p-hydroxymethylphenyl)-3-methoxyacrylate in 20 ml of acetone. The mixture is allowed to reach room temperature and a further 3 ml of Jones reagent are added to the greenish solution, after which a permanent orange color is obtained.
The excess oxidizing agent is decomposed by adding a little methanol, the precipitated greenish solid is filtered off under suction and the solvent is evaporated under reduced pressure. The residue is taken up in CH 2 Cl 2 and the organic phase is extracted twice with water, dried over MgSO 4 and evaporated down.
The residue is purified by column chromatography, after which 0.8 g (3.4 mmol, 34%) of the title compound is obtained.
1 H-NMR (CDCl 3 ): δ: 3.75 (s, 3H) ; 3. 9 (s, 3H) ; 7.45 (d, J=8Hz, 2H) ; 7.6 (s, 1H); 8.1 (d, J=8Hz, 2H); 11.4 (s, broad, 1H).
›EXAMPLE 19 · 1 of 5
Methyl 2-(p-carboxymethylphenyl)-3-methoxyacrylate (Table 3, Number 26)
0.3 g (12.5 mmol) of sodium hydride is added a little at a time to 1 g (4 mmol) of methyl 2-(p-carboxyphenyl)-3-methoxyacrylate in 10 ml of dimethylformamide. Stirring is carried out for 30 minutes at room temperature, after which 1.3 g (10 mmol) of dimethyl sulfate are added. Stirring is continued for a further 30 minutes, the mixture is diluted with 100 ml of 1% strength NH 4 OH solution and the aqueous phase is extracted with methylene chloride. The solvent is evaporated off, the residue is taken up in ether and the ether-insoluble residue is filtered off under suction and discarded.
The organic phase is washed with water, dried over MgSO 4 and evaporated down.
Purification of the residue by column chromatography gives 0.5 g (2 mmol, 50%) of the title compound as colorless crystals (mp.=81°-84° C.).
1 H-NMR (CDCl 3 ): δ=3.75 (s, 3H); 3.9 (s, 3H); 3.95 (s, 3H); 7.45 (d, J=8Hz, 2H); 7.6 (s, 1H); 8.05 (d, J=8Hz, 2H).
__________________________________________________________________________
##STR28##
No. U Y mp NMR: δ (ppm)
__________________________________________________________________________
1 O 3-CH.sub.3
oil 2.4(S, 3H,); 4.0(S, 3H)
2 O 3-CH.sub.2 Br
oil 4.0(S, 3H); 4.5(S, 2H)
3 O 3-CH.sub.2 Cl
4 O 3-CHO
5 O 3-COOH
6 O 3-PO(OCH.sub.3).sub.2
7 O 3-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-
8 O 3-CH.sub.2 OH
9 O 4-CH.sub.2 Br
10 O 4-CH.sub.2 Cl
11 O 4-CHO
12 O 4-COOH
13 O 4-PO(OCH.sub.3).sub.2
14 O 4-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-
15 O 4-CH.sub.2 OH
16 HCOCH.sub.3
3-CH.sub.3
58-61
17 HCOCH.sub.3
3-CH.sub.2 Br
90-91
18 HCOCH.sub.3
3-CH.sub.2 Cl
19 HCOCH.sub.3
3-CHO oil 7.6(S, 1H); 10.0(S, 1H)
20 HCOCH.sub.3
3-COOH 158-162
21 HCOCH.sub.3
3-OH 94-96
22 HCOCH.sub.3
3-PO(OCH.sub.3).sub.2
93- 94
23 HCOCH.sub.3
3-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-
24 HCOCH.sub.3
3-CH.sub.2 OH
oil 4.6(S, 1H); 7.55(S, 1H)
25 HCOCH.sub.3
4-CH.sub.3
62-63
26 HCOCH.sub.3
4-CH.sub.2 Br
76-81
27 HCOCH.sub.3
4-CH.sub.2 Cl
28 HCOCH.sub.3
4-CHO
29 HCOCH.sub.3
4-COOH 158-162
30 HCOCH.sub.3
4-OH 107-109
31 HCOCH.sub.3
4-PO(OCH.sub.3).sub.2
32 HCOCH.sub.3
4-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-
33 HCOCH.sub.3
4-CH.sub.2 OH
62-63
34a) NOCH.sub.3
3-CH.sub.3
oil 2.35(S, 3H); 3.9(S, 3H);
non-polar isomer 4.0(S, 3H)
34b) NOCH.sub.3
3-CH.sub.3
66-67
polar isomer
35a) NOCH.sub.3
3-CH.sub.2 Br
74-75
non-polar isomer
35b) NOCH.sub.3
3-CH.sub.2 Br
68-69
36 NOCH.sub.3
3-CH.sub.2 Cl
37 NOCH.sub.3
3-CHO
38 NOCH.sub.3
3-COOH
39 NOCH.sub.3
3-PO(OCH.sub.3).sub.2
40 NOCH.sub.3
3-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-
41 NOCH.sub.3
3-CH.sub.2 .sup.- OH
42 NOCH.sub.3
4-CH.sub.3
43 NOCH.sub.3
4-CH.sub.2 Br
44 NOCH.sub.3
4-CH.sub.2 Cl
45 NOCH.sub.3
4-CHO
46 NOCH.sub.3
4-COOH
47 NOCH.sub.3
4-PO(OCH.sub.3).sub.2
48 NOCH.sub.3
4-P.sup.+ (C.sub.6 H.sub.5).sub.3 Cl.sup.-
49 NOCH.sub.3
4-CH.sub.2 OH
50 CHCH.sub.3
3-CH.sub.3
51 CHCH.sub.3
3-CH.sub.2 Br
52 CHCH.sub.3
3-CH.sub.2 Cl
53 CHCH.sub.3
3-CHO
54 CHCH.sub.3
3-COOH
55 CHCH.sub.3
3-OH
56 CHCH.sub.3
3-PO(OCH.sub.3).sub.2
57 CHCH.sub.3
3-P.sup.+ (C.sub.6 H.sub.5).sub.3 .sup.- Cl
58 CHCH.sub.3
3-CH.sub.2 OH
59 CHCH.sub.3
4-CH.sub.3
60 CHCH.sub.3
4-CH.sub.2 Br
61 CHCH.sub.3
4-CH.sub.2 Cl
62 CHCH.sub.3
4-CHO
63 CHCH.sub.3
4-COOH
64 CHCH.sub.3
4-OH
65 CHCH.sub.3
4-PO(OCH.sub.3).sub.2
66 CHCH.sub.3
4-P.sup.+ (C.sub.6 H.sub.5).sub.3 .sup.- Cl
67 CHCH.sub.3
4-CH.sub.2 OH
__________________________________________________________________________
TABLE 2
##STR29##
No. U A B mp NMR: δ
(ppm) 1 HCOCH.sub.3 CH.sub.2
CH.sub.2 H 2 HCOCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 3 HCOCH.sub.3
CH.sub.2 CH.sub.2 cyclohexyl 4 HCOCH.sub.3 CH.sub.2 CH.sub.2 phenyl oil
2.95(S, 4H); 7.55(S, 1H) 5 HCOCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 6
HCOCH.sub.3 CHCH H 7 HCOCH.sub.3 CHCH CH.sub.3 8 HCOCH.sub.3 CHCH
cyclohexyl 9 HCOCH.sub.3 CHCH 2-naphthyl 10 HCOCH.sub.3 CHCH 2-pyridyl
11 HCOCH.sub.3 OCH.sub.2 H oil 3.7; 3, 78; 3.82(3S, 9H); 7.55(S,
1H) 12 HCOCH.sub.3 OCH.sub.2 CH.sub.3 43-45 13 HCOCH.sub.3 OCH.sub.2
cyclohexyl 14 HCOCH.sub.3 OCH.sub.2 phenyl oil 5.05(S, 2H); 7.55(S, 1H)
15 HCOCH.sub.3 O CH.sub.2 2-pyridyl 16 HCOCH.sub.3 OCH.sub.2 CO H 17
HCOCH.sub.3 OCH.sub.2 CO CH.sub.3 18 HCOCH.sub.3 OCH.sub.2
CO cyclohexyl 19 HCOCH.sub.3 OCH.sub.2 CO phenyl 103-105
20 HCOCH.sub.3 OCH.sub.2 CO 2-pyridyl 21 HCOCH.sub.3 CH.sub.2 OCO H
oil 5.2(S, 2H); 7.55(S, 1H) 22 HCOCH.sub.3 CH.sub.2 OCO CH.sub.3 34-35
23 HCOCH.sub.3 CH.sub.2 OCO cyclohexyl 24 HCOCH.sub.3 CH.sub.2 OCO
phenyl oil 5.4(S, 2H); 7.6(S, 1H) 25 HCOCH.sub.3 CH.sub.2 OCO 2-pyridyl
26 HCOCH.sub.3 COOCH.sub.2 H 27 HCOCH.sub.3 COOCH.sub.2 CH.sub.3 28
HCOCH.sub.3 COOCH.sub.2 cyclohexyl 29 HCOCH.sub.3 COOCH.sub.2 phenyl
30 HCOCH.sub.3 COOCH.sub.2 2-pyridyl 31 HCOCH.sub.3 OCOCH.sub.2 H 32
HCOCH.sub.3 OCOCH.sub.2 CH.sub.3 33 HCOCH.sub.3 OCOCH.sub.2 cyclohexyl
34 HCOCH.sub.3 OCOCH.sub. 2 phenyl 65-66 35 HCOCH.sub.3 OCOCH.sub.2
2-pyridyl 36 HCOCH.sub.3 OCO phenyl 98-99 37 HCOCH.sub.3 OCH.sub.2 COO
CH.sub.3 51-53 38 HCOCH.sub.3 O(CH.sub.2).sub.3 COO CH.sub.3 oil 4.0(t,
J=7Hz, 3H); 7.55(S, 1H) 39 HCOCH.sub.3 O(CH.sub.2).sub.7 COO CH.sub.3
oil 3.95(t, J=7Hz, 2H); 7.55(S, 1H) 40 HCOCH.sub.3 O(CH.sub.2).sub.2 O
H oil 4.1(t, J=5Hz, 2H), 7.55(S, 1H) 41 HCOCH.sub.3 O(CH.sub.2).sub.2 O
CH.sub.3 42 HCOCH.sub.3 O(CH.sub.2).sub.2 O cyclohexyl 43 HCOCH.sub.3 (
OCH.sub.2).sub.2 O phenyl oil 4.3(S, 4H); 7.55(S, 1H) 44 HCOCH.sub.3
O(CH.sub.2).sub.2 O 2-pyridyl 45 HCOCH.sub.3 O(CH.sub.2).sub.3 O H oil
4.1(t, J=6Hz, 2H), 7.55(S, 1H) 46 HCOCH.sub.3 O(CH.sub.2).sub.3 O
CH.sub.3 47 HCOCH.sub.3 O(CH.sub.2).sub.3 O cyclohexyl 47 HCOCH.sub.3 (
OCH.sub.2 ).sub.3 O cyclohexyl 48 HCOCH.sub.3 O(CH.sub.2).sub.3 O
phenyl 68-69 49 HCOCH.sub.3 O(CH.sub.2).sub.3 O 2-pyridyl
50 HCOCH.sub.3 O(CH.sub.2).sub.4 O H oil 4.0(t, J=6Hz, 2H); 7.55(S, 1H)
51 HCOCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3
52 HCOCH.sub.3 O(CH.sub.2).sub.4 O cyclohexyl
53 HCOCH.sub.3 O(CH.sub.2).sub.4 O phenyl 92-93 54 HCOCH.sub.3
O(CH.sub.2).sub.4 O 2-pyridyl 55 HCOCH.sub.3 O(CH.sub.2).sub.5 O H 56
HCOCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3
57 HCOCH.sub.3 O(CH.sub.2).sub.5 O cyclohexyl
58 HCOCH.sub.3 O(CH.sub.2).sub.5 O phenyl oil 4.0(t, J=6Hz, 4H);
7.55(S, 1H) 59 HCOCH.sub.3 O(CH.sub.2).sub.5 O 2-pyridyl
›EXAMPLE 19 · 2 of 5
60 HCOCH.sub.3 O(CH.sub.2).sub.6 O H 61 HCOCH.sub.3 O(CH.sub.2).sub.6
O CH.sub.3 62 HCOCH.sub.3 O(CH.sub. 2).sub.6 O cyclohexyl
63 HCOCH.sub.3 O(CH.sub.2).sub.6 O phenyl 78-80 64 HCOCH.sub.3
O(CH.sub.2).sub.6 O 2-pyridyl 65 HCOCH.sub.3 O(CH.sub.2).sub.8 O H oil
3.95(t, J=6Hz, 2H); 7.55(S, 1H) 66 HCOCH.sub.3 O(CH.sub.2).sub.8 O
CH.sub.3 67 HCOCH.sub.3 O(CH.sub.2).sub.8 O cyclohexyl 68 HCOCH.sub.3 (
OCH.sub.2).sub.8 O phenyl 69-74 69 HCOCH.sub.3 O(CH.sub.2).sub.8 O
2-pyridyl 70 HCOCH.sub.3 O(CH.sub.2).sub.10 O H 71 HCOCH.sub.3
O(CH.sub.2).sub.10 O CH.sub.3 72 HCOCH.sub.3 O(CH.sub.2).sub.10 O
cyclohexyl 73 HCOCH.sub.3 O(CH.sub.2).sub.10 O phenyl 49-52 74
HCOCH.sub.3 O(CH.sub.2).sub.10 O 2-pyridyl 75 HCOCH.sub.3 CH.sub.2 O
CH.sub.3 76 HCOCH.sub.3 CH.sub.2 O cyclohexyl 77 HCOCH.sub.3 CH.sub.2
O phenyl 72-74 78 HCOCH.sub.3 CH.sub. 2 O pyridyl 79 HCOCH.sub.3
CH.sub.2 SCH.sub.2 phenyl oil 3.55(S, 4H); 7.55(S, 1H) 80 HCOCH.sub.3
CH.sub.2 S H 81 HCOCH.sub.3 CH.sub.2 S CH.sub.3 82 HCOCH.sub.3
CH.sub.2 S cyclohexyl 83 HCOCH.sub.3 CH.sub.2 S phenyl 69-70 84
HCOCH.sub.3 CH.sub.2 S 2-pyridyl oil 4.45(S, 2H); 7.55(S, 1H) 85
HCOCH.sub.3 CH.sub.2 N(CH.sub.3) H 86 HCOCH.sub.3 CH.sub.2 N(CH.sub.3)
CH.sub.3 87 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) cyclohexyl 88 HCOCH.sub.3
CH.sub.2 N(CH.sub.3) phenyl oil 3.65(S, 3H); 3.75(S, 3H); 4.55(S,
2H) 89 HCOCH.sub.3 CH.sub.2 N(CH.sub.3) 2-pyridyl 90 HCOCH.sub.3 O
CH(CN)COCH.sub.2 H 91 HCOCH.sub.3 CH(CN)OCOCH.sub.2 CH.sub.3 92
HCOCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl
93 HCOCH.sub.3 CH(CN)OCOCH.sub.2 phenyl
94 HCOCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl 95 HCOCH.sub.3 CH(CN)OCO
phenyl oil 6.7(S, 1H); 7.6(S, 1H) 96 HCOCH.sub.3 CHN H 97 HCOCH.sub.3
CHN CH.sub.3 98 HCOCH.sub.3 CHN cyclohexyl 99 HCOCH.sub.3 CHN phenyl
100 HCOCH.sub.3 CHN 2-pyridyl 101 HCOCH.sub.3 CHNOCH.sub.2 H 102
HCOCH.sub.3 CHNOCH.sub.2 CH.sub.3 103 HCOCH.sub.3 CHNOCH.sub.2 cyclohexyl
104 HCOCH.sub.3 CHNOCH.sub.2 phenyl 105 HCOCH.sub.3 CHNOCH.sub.2
2-pyridyl 106 NOCH.sub.3 CH.sub.2 CH.sub.2 H 107 NOCH.sub.3 CH.sub.2
CH.sub.2 CH.sub.3 108 NOCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 109
NOCH.sub.3 CH.sub.2 CH.sub.2 phenyl 110 NOCH.sub.3 CH.sub.2 CH.sub.2
2-pyridyl 111 NOCH.sub.3 CHCH H 112 NOCH.sub.3 CHCH CH.sub.3 113
NOCH.sub.3 CHCH cyclohexyl 114 NOCH.sub.3 CHCH phenyl 115 NOCH.sub.3
CHCH 2-pyridyl 116 NOCH.sub.3 OCH.sub.2 H 117 NOCH.sub.3 OCH.sub.2
CH.sub.3 118 NOCH.sub.3 OCH.sub.2 cyclohexyl 119a) NOCH.sub.3 OCH.sub.2
phenyl 62-63 non-polar isomer 3.9(S, 3H); 4.0(S, 3H); 5.05(S, 2H)
119b) NOCH.sub.3 OCH.sub.2 phenyl 63-64 polar isomer 3.85(S, 3H),
4.05(S, 3H); 5.05(S, 2H) 120 NOCH.sub.3 OCH.sub.2 2-pyridyl 121
NOCH.sub.3 OCH.sub.2 CO H 122 NOCH.sub.3 OCH.sub.2 CO CH.sub.3 123
NOCH.sub.3 OCH.sub.2 CO cyclohexyl 124 NOCH.sub.3 OCH.sub.2 CO phenyl
125 NOCH.sub.3 OCH.sub.2 CO 2-pyridyl 126 NOCH.sub.3 CH.sub.2 OCO H 127
NOCH.sub.3 CH.sub.2 OCO CH.sub.3 128 NOCH.sub.3 CH.sub.2 OCO cyclohexyl
129 NOCH.sub.3 CH.sub.2 OCO phenyl 130 NOCH.sub.3 CH.sub.2 OCO 2-pyridyl
131 NOCH.sub.3 COOCH.sub.2 H 132 NOCH.sub.3 COOCH.sub.2 CH.sub.3 133
NOCH.sub.3 COOCH.sub.2 cyclohexyl 134 NOCH.sub.3 COOCH.sub.2 phenyl 135
NOCH.sub.3 COOCH.sub.2 2-pyridyl 136 NOCH.sub.3 OCOCH.sub.2 H 137
NOCH.sub.3 OCOCH.sub.2 CH.sub.3 138 NOCH.sub.3 OCOCH.sub.2 cyclohexyl
139 NOCH.sub.3 OCOCH.sub.2 phenyl 140 NOCH.sub.3 OCOCH.sub.2 2-pyridyl
141 NOCH.sub.3 OCO phenyl 142 NOCH.sub.3 OCH.sub.2 COO CH.sub.3 143
NOCH.sub.3 O(CH.sub.2).sub.3
COO CH.sub.3 144 NOCH.sub.3 O(CH.sub.2).sub.7
COO CH.sub.3 145 NOCH.sub.3 O(CH.sub.2).sub.2 O H 146 NOCH.sub.3
O(CH.sub.2).sub.2 O CH.sub.3 147 NOCH.sub.3 O(CH.sub.2).sub.2
O cyclohexyl 148 NOCH.sub.3 O(CH.sub.2).sub.2 O phenyl 149 NOCH.sub.3
O(CH.sub.2).sub.2 O 2-pyridyl 150 NOCH.sub.3 O(CH.sub.2).sub.3 O H 151
NOCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3 152 NOCH.sub.3 O(CH.sub.2).sub.3 O
cyclohexyl 153 NOCH.sub.3 O(CH.sub.2).sub.3 O phenyl 154 NOCH.sub.3
O(CH.sub.2).sub.3 O 2-pyridyl 155 NOCH.sub.3 O(CH.sub.2).sub.4 O H 156
NOCH.sub.3 O(CH.sub.2).sub.4
O CH.sub.3 157 NOCH.sub. 3 O(CH.sub.2).sub.4
O cyclohexyl 158 NOCH.sub.3 O(CH.sub.2).sub.4 O phenyl 159 NOCH.sub.3
O(CH.sub.2).sub.4 O 2-pyridyl 160 NOCH.sub.3 O(CH.sub.2).sub.5 O H 161
NOCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3 162 NOCH.sub.3 O(CH.sub.2).sub.5 O
cyclohexyl 163 NOCH.sub.3 O(CH.sub.2).sub.5 O phenyl 164 NOCH.sub.3
O(CH.sub.2).sub.5 O 2-pyridyl 165 NOCH.sub.3 O(CH.sub.2).sub.6 O H 166
NOCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3 167 NOCH.sub.3 O(CH.sub.2).sub.6 O
cyclohexyl 168 NOCH.sub.3 O(CH.sub.2).sub.6 O phenyl 169 NOCH.sub.3
O(CH.sub.2).sub.6 O 2-pyridyl 170 NOCH.sub.3 O(CH.sub.2).sub.8 O H 171
NOCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3 172 NOCH.sub.3 O(CH.sub.2).sub.8 O
cyclohexyl 173 NOCH.sub.3 O(CH.sub.2).sub.8 O phenyl 174 NOCH.sub.3
O(CH.sub.2).sub.8 O 2-pyridyl 175 NOCH.sub.3 O(CH.sub.2).sub.10 O H 176
NOCH.sub.3 O(CH.sub.2).sub.10
O CH.sub.3 177 NOCH.sub.3 O(CH.sub.2).sub.10
O cyclohexyl 178 NOCH.sub.3 O(CH.sub.2).sub.10 O phenyl 179 NOCH.sub.3 (
OCH.sub.2).sub.10 O 2-pyridyl 180 NOCH.sub.3 CH.sub.2 O H 181 NOCH.sub.3
CH.sub.2 O CH.sub.3 182 NOCH.sub.3 CH.sub.2 O cyclohexyl 183 NOCH.sub.3
CH.sub.2 O phenyl 184 NOCH.sub.3 CH.sub.2 O pyridyl 185 NOCH.sub.3
CH.sub.2 SCH.sub.2 H 186 NOCH.sub.3 CH.sub.2 SCH.sub.2 CH.sub.3 187
NOCH.sub.3 CH.sub.2 SCH.sub.2 cyclohexyl 188 NOCH.sub.3 CH.sub.2
SCH.sub.2 phenyl 189 NOCH.sub.3 CH.sub.2 SCH.sub.2 2-pyridyl 190
NOCH.sub.3 CH.sub.2 N(CH.sub.3) H 191 NOCH.sub.3 CH.sub.2 N(CH.sub.3)
CH.sub.3 192 NOCH.sub.3 CH.sub.2 N(CH.sub.3) cyclohexyl 193 NOCH.sub.3
CH.sub.2 N(CH.sub.3) phenyl 194 NOCH.sub.3 CH.sub.2 N(CH.sub. 3)
2-pyridyl 195 NOCH.sub.3 CH(CN)OCOCH.sub.2 H 196 NOCH.sub.3 CH(CN)OCOCH.s
ub.2 CH.sub.3 197 NOCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl 198 NOCH.sub.3
CH(CN)OCOCH.sub.2 phenyl 199 NOCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl 200
NOCH.sub.3 CH(CN)OCO phenyl 201 NOCH.sub.3 CHN H 202 NOCH.sub.3 CHN
CH.sub.3 203 NOCH.sub.3 CHN cyclohexyl 204 NOCH.sub.3 CHN phenyl 205
NOCH.sub.3 CHN 2-pyridyl 206 NOCH.sub.3 CHNOCH.sub.2 H 207 NOCH.sub.3 O
C
CHNH.sub.2 CH.sub.3 208 NOCH.sub.3 CHNOCH.sub.2 cyclohexyl 209 NOCH.sub.3
CHNOCH.sub.2 phenyl 210 NOCH.sub.3 CHNOCH.sub.2 2-pyridyl 211 HCCH.sub.3
›EXAMPLE 19 · 3 of 5
CH.sub.2 CH.sub.2 H 212 HCCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 213
HCCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 214 HCCH.sub.3 CH.sub.2 CH.sub.2
phenyl 215 HCCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 216 HCCH.sub.3 CHCH H
217 HCCH.sub.3 CHCH CH.sub.3 218 HC CH.sub.3 CHCH cyclohexyl 219
HCCH.sub.3 CHCH phenyl 220 HCCH.sub.3 CHCH 2-pyridyl 221 HCCH.sub.3
OCH.sub.2 H 222 HCCH.sub.3 OCH.sub.2 CH.sub.3 223 HCCH.sub.3 OCH.sub.2
cyclohexyl 224 HCCH.sub.3 OCH.sub.2 phenyl 225 HCCH.sub.3 OCH.sub.2
2-pyridyl 226 HCCH.sub.3 OCH.sub.2 CO H 227 HCCH.sub.3 OCH.sub.2 CO
CH.sub.3 228 HCCH.sub.3 OCH.sub.2 CO cyclohexyl 229 HCCH.sub.3 OCH.sub.2 C
O phenyl 230 HCCH.sub.3 OCH.sub.2 CO 2-pyridyl 231 HCCH.sub.3 CH.sub.2
OCO H 232 HCCH.sub.3 CH.sub.2 OCO CH.sub.3 233 HCCH.sub.3 CH.sub.2 OCO
cyclohexyl 234 HCCH.sub.3 CH.sub.2 OCO phenyl 235 HCCH.sub.3 CH.sub.2
OCO 2-pyridyl 236 HCCH.sub.3 COOCH.sub.2 H 237 HCCH.sub.3 COOCH.sub.2
CH.sub.3 238 HCCH.sub.3 COOCH.sub.2 cyclohexyl 239 HCCH.sub.3 COOCH.sub.2
phenyl 240 HCCH.sub.3 COO CH.sub.2 2-pyridyl 241 HCCH.sub.3 OCOCH.sub.2
H 242 HCCH.sub.3 OCOCH.sub.2 CH.sub.3 243 HCCH.sub.3 OCOCH.sub.2
cyclohexyl 244 HCCH.sub.3 OCOCH.sub.2 phenyl 245 HCCH.sub.3 OCOCH.sub.2
2-pyridyl 246 HCCH.sub.3 OCO phenyl 247 HCCH.sub.3 OCOCOO CH.sub.3 248 C
HCH.sub.3 O(CH.sub.2).sub.3
COO CH.sub.3 249 HCCH.sub.3 O(CH.sub.2).sub.3
COO CH.sub.3 250 HCCH.sub.3 O(CH.sub.2).sub.2 O H 251 HCCH.sub.3
O(CH.sub.2).sub.2 O CH.sub.3 252 HCCH.sub.3 O(CH.sub.2).sub.2
O cyclohexyl 253 HCCH.sub.3 O(CH.sub.2).sub.2 O phenyl 254 HCCH.sub.3
O(CH.sub.2).sub.2 O 2-pyridyl 255 HCCH.sub.3 O(CH.sub.2).sub.3 O H 256 C
HCH.sub.3 O(CH.sub.2).sub.3 O CH.sub.3 257 HCCH.sub.3 O(CH.sub.2).sub.3
O cyclohexyl 258 HCCH.sub.3 O(CH.sub.2).sub.3 O phenyl 259 HCCH.sub.3
O(CH.sub.2).sub.3 O 2-pyridyl 260 HCCH.sub.3 O(CH.sub.2).sub.4 O H 261 C
HCH.sub.3 O(CH.sub.2).sub.4 O CH.sub.3 262 HCCH.sub.3 O(CH.sub.2).sub.4
O cyclohexyl 263 HCCH.sub.3 O(CH.sub.2).sub.4 O phenyl 264 HCCH.sub.3
O(CH.sub.2).sub.4 O 2-pyridyl 265 HCCH.sub.3 O(CH.sub.2).sub.5 O H 266 C
HCH.sub.3 O(CH.sub.2).sub.5 O CH.sub.3 267 HCCH.sub.3 O(CH.sub.2).sub.5
O cyclohexyl 268 HCCH.sub.3 O(CH.sub.2).sub.5 O phenyl 269 HCCH.sub.3
O(CH.sub.2).sub.5 O 2-pyridyl 270 HCCH.sub.3 O(CH.sub.2).sub.6 O H 271 C
HCH.sub.3 O(CH.sub.2).sub.6 O CH.sub.3 272 HCCH.sub.3 O(CH.sub.2).sub.6
O cyclohexyl 273 HCCH.sub.3 O(CH.sub.2).sub.6 O phenyl 274 HCCH.sub.3
O(CH.sub.2).sub.6 O 2-pyridyl 275 HCCH.sub. 3 O(CH.sub.2).sub.8 O H 276
HCCH.sub.3 O(CH.sub.2).sub.8 O CH.sub.3 277 HCCH.sub.3 O(CH.sub.2).sub.8 O
cyclohexyl 278 HCCH.sub.3 O(CH.sub.2).sub.8 O phenyl 279 HCCH.sub.3
O(CH.sub.2).sub.8 O 2-pyridyl 280 HCCH.sub.3 O(CH.sub.2).sub.10 O H 281
HCCH.sub.3 O(CH.sub.2).sub.10
O CH.sub.3 282 HCCH.sub.3 O(CH.sub.2).sub.10
O cyclohexyl 283 HCCH.sub.3 O(CH.sub.2).sub.10 O phenyl 284 HCCH.sub.3 (
OCH.sub.2).sub.10 O 2-pyridyl 285 HCCH.sub.3 CH.sub.2 O H 286 HCCH.sub.3
CH.sub.2 O CH.sub.3 287 HCCH.sub.3 CH.sub.2 O cyclohexyl 288 HCCH.sub.3
CH.sub.2 O phenyl oil 1.75(d, J=8Hz, 3H); 3.75/S, 3H); 5.1(S, 2H)
289 HCCH.sub.3 CH.sub.2 O pyridyl 290 HCCH.sub.3 CH.sub.2 SCH.sub.2 H
291 HCCH.sub.3 CH2 SCH2 CH3 292 HCCH.sub.3 CH2SCH2 cyclohexyl 293
HCCH.sub.3 CH2SCH2 phenyl 294 HCCH.sub.3 CH2SCH2 2-pyridyl 295 HCCH.sub.3
CH2N(CH3) H 296 HCCH.sub.3 CH2N(CH3) CH3 297 HCCH.sub.3 CH2N(CH3)
cyclohexyl 298 HCCH.sub.3 CH2N(CH3) phenyl 299 HCCH.sub.3 CH2N(CH3)
2-pyridyl 300 HCCH.sub.3 CH(CN)OCOCH.sub.2 H 301 HCCH.sub.3 CH(CN)OCOCH.s
ub.2 CH.sub.3 302 HCCH.sub.3 CH(CN)OCOCH.sub.2 cyclohexyl 303 HCCH.sub.3
CH(CN)OCOCH.sub.2 phenyl 304 HCCH.sub.3 CH(CN)OCOCH.sub.2 pyridyl 305
HCCH.sub.3 CH(CN)OCO phenyl 306 HCCH.sub.3 CHN H 307 HCCH.sub.3 CHN
CH.sub.3 308 HCCH.sub.3 CHN cyclohexyl 309 HCCH.sub.3 CHN phenyl 310
HCCH.sub.3 CHN 2-pyridyl 311 HCCH.sub.3 CHNOCH.sub.2 H 312 HCCH.sub.3 O
C
CHNH.sub.2 CH.sub.3 313 HCCH.sub.3 CHNOCH.sub.2 cyclohexyl 314 HCCH.sub.3
CHNOCH.sub.2 phenyl 315 HCCH.sub.3 CHNOCH.sub.2 2-pyridyl 316 O
CH.sub.2 CH.sub.2 H 317 O CH.sub.2 CH.sub.2 CH.sub.3 318 O CH.sub.2
CH.sub.2 cyclohexyl 319 O CH.sub.2 CH.sub.2 phenyl 320 O CH.sub.2
CH.sub.2 2-pyridyl 321 O CHCH H 322 O CHCH CH.sub.3 323 O CHCH cyclohexyl
324 O CHCH phenyl 325 O CHCH 2-pyridyl 326 O OCH.sub.2 H 327 O OCH.sub.2
CH.sub.3 328 O OCH.sub.2 cyclohexyl 329 O OCH.sub.2 phenyl 330 O
OCH.sub.2 2-pyridyl 331 O CH.sub.2 O H 332 O CH.sub.2 O CH.sub.3 333 O
CH.sub.2 O cyclohexyl 334 O CH.sub.2 O phenyl 335 O CH.sub.2 O 2-pyridyl
336 O CH.sub.2 OCO H 337 O CH.sub.2 OCO CH.sub.3 338 O CH.sub.2 OCO
cyclohexyl 339 O CH.sub.2 OCO phenyl 340 O CH.sub.2 OCO 2-pyridyl 341
NNHCH.sub.3 CH.sub.2 CH.sub.2 H 342 NNHCH.sub.3 CH.sub.2 CH.sub.2
CH.sub.3 343 NNHCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 344 NNHCH.sub.3
CH.sub.2 CH.sub.2 phenyl 345 NNHCH.sub.3 CH.sub.2 CH.sub.2 2-pyridyl 346
NNHCH.sub.3 CHCH H 347 NNHCH.sub.3 CHCH CH.sub.3 348 NNHCH.sub.3 CHCH
cyclohexyl 349 NNHCH.sub.3 CHCH phenyl 350 NNHCH.sub.3 CHCH 2-pyridyl
351 NNHCH.sub.3 OCH.sub.2 H 352 NNHCH.sub.3 OCH.sub.2 CH.sub.3 353
NNHCH.sub.3 OCH.sub.2 cyclohexyl 354 NNHCH.sub.3 OCH.sub.2 phenyl 355
NNHCH.sub.3 OCH.sub.2 2-pyridyl 356 NNHCH.sub.3 CH.sub.2 O H 357
NNHCH.sub.3 CH.sub.2 O CH.sub.3 358 NNHCH.sub.3 CH.sub.2 O cyclohexyl
359 NNHCH.sub.3 CH.sub.2 O phenyl 360 NNHCH.sub.3 CH.sub.2 O 2-pyridyl
361 NNHCH.sub.3 CH.sub.2 OCO H 362 NNHCH.sub.3 CH.sub.2 OCO CH.sub.3 363
NNHCH.sub.3 CH.sub.2 OCO cyclohexyl 364 NNHCH.sub.3 CH.sub.2 OCO phenyl
365 NNHCH.sub.3 CH.sub.2 OCO 2-pyridyl 366 CH.sub.2 CH.sub.2 CH.sub.2 H
367 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 368 CH.sub.2 CH.sub.2 CH.sub.2
cyclohexyl 369 CH.sub.2 CH.sub.2 CH.sub.2 phenyl 370 CH.sub.2 CH.sub.2
CH.sub.2 2-pyridyl 371 CH.sub.2 CHCH H 372 CH.sub.2 CHCH CH.sub.3 373
CH.sub.2 CHCH cyclohexyl 374 CH.sub.2 CHCH phenyl 375 CH.sub.2 CHCH
2-pyridyl 376 CH.sub.2 OCH.sub.2 H 377 CH.sub.2 OCH.sub.2 CH.sub.3 378
CH.sub.2 OCH.sub.2 cyclohexyl 379 CH.sub.2 OCH.sub.2 phenyl 380 CH.sub.2
OCH.sub.2 2-pyridyl 381 CH.sub.2 CH.sub.2 O H 382 CH.sub.2 CH.sub.2 O
CH.sub.3 383 CH.sub.2 CH.sub.2 O cyclohexyl 384 CH.sub.2 CH.sub.2 O
phenyl 385 CH.sub.2 CH.sub.2 O 2-pyridyl 386 CH.sub.2 CH.sub.2 OCO H 387
›EXAMPLE 19 · 4 of 5
CH.sub.2 CH.sub.2 OCO CH.sub.3 388 CH.sub.2 CH.sub.2 OCO cyclohexyl 389
CH.sub.2 CH.sub.2 O CO phenyl 390 CH.sub.2 CH.sub.2 OCO 2-pyridyl 391
CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 H 392 CHCH.sub.2 CH.sub.3 CH.sub.2 C
H.sub.2 CH.sub.3 393 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl
394 CHCH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 phenyl 395 CHCH.sub.2 CH.sub.3
CH.sub.2 CH.sub.2 2-pyridyl 396 CHCH.sub.2
CH.sub.3 CHCH H 397 CHCH.sub.2 CH.sub.3 CHCH CH.sub.3 398 CHCH.sub.2
CH.sub.3 CHCH cyclohexyl 399 CHCH.sub.2 CH.sub.3 CHCH phenyl 400
CHCH.sub.2 CH.sub.3 CHCH 2-pyridyl 401 CHCH.sub.2 CH.sub.3 OCH.sub.2 H
402 CHCH.sub.2 CH.sub.3 OCH.sub.2 CH.sub.3 403 CHCH.sub.2 CH.sub.3
OCH.sub.2 cyclohexyl 404 CHCH.sub.2 CH.sub.3 OCH.sub.2 phenyl 405
CHCH.sub.2 CH.sub.3 OCH.sub.2 2-pyridyl 406 CHCH.sub.2 CH.sub.3 CH.sub.2 O
H 407 CHCH.sub.2 CH.sub.3 CH.sub.2 O CH.sub.3 408 CHCH.sub.2 CH.sub.3
CH.sub.2 O cyclohexyl 409 CHCH.sub.2 CH.sub.3 CH.sub.2 O phenyl 410
CHCH.sub.2 CH.sub.3 CH.sub.2 O 2-pyridyl 411 CHCH.sub.2 CH.sub.3
CH.sub.2 OCO H 412 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO CH.sub.3 413
CHCH.sub.2 CH.sub.3 CH.sub.2 OCO cyclohexyl 414 CHCH.sub.2 CH.sub.3
CH.sub.2 OCO phenyl 415 CHCH.sub.2 CH.sub.3 CH.sub.2 OCO 2-pyridyl 416 S
C
CHH.sub.3 CH.sub.2 CH.sub.2 H 417 CHSCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3
418 CHSCH.sub.3 CH.sub.2 CH.sub.2 cyclohexyl 419 CHSCH.sub.3 CH.sub.2
CH.sub.2 phenyl 420 CHSCH.sub.3 CH.sub.2
CH.sub.2 2-pyridyl 421 CHSCH.sub.3 CHCH H 422 CHSCH.sub.3 CHCH CH.sub.3
423 CHSCH.sub.3 CHCH cyclohexyl 424 CHSCH.sub.3 CHCH phenyl 425 CHSCH.sub
.3 CHCH 2-pyridyl 426 CHSCH.sub.3 OCH.sub.2 H 427 CHSCH.sub.3 OCH.sub.2
CH.sub.3 428 CHSCH.sub.3 OCH.sub.2 cyclohexyl 429 CHSCH.sub.3 OCH.sub.2
phenyl 430 CHSCH.sub.3 OCH.sub.2 2-pyridyl 431 CHSCH.sub.3 CH.sub.2 O H
432 CHSCH.sub.3 CH.sub.2 O CH.sub.3 433 CHSCH.sub.3 CH.sub.2
O cyclohexyl 434 CHSCH.sub.3 CH.sub.2 O phenyl 435 CHSCH.sub.3 CH.sub.2 O
2-pyridyl 436 CHSCH.sub.3 CH.sub.2 OCO H 437 CHSCH.sub.3 CH.sub.2 OCO
CH.sub.3 438 CHSCH.sub.3 CH.sub.2 OCO cyclohexyl 439 CHSCH.sub.3
CH.sub.2 OCO phenyl 440 CHSCH.sub.3 CH.sub.2
OCO 2-pyridyl 441 HCOCH.sub.3 CH.sub.2 OCO 1-(4-methoxy- 66-69
phenyl)-cyclopropyl 442 HCOCH.sub.3 CH.sub.2 OCO 2-pyridyl 70-74 443
HCOCH.sub.3 CH.sub.2 OCO 3-pyridyl 444 HCOCH.sub.3 CH.sub. 2 OCO
4-pyridyl oil 5.45(S, 2H); 7.55(S, 1H) 445 HCOCH.sub.3 CH.sub.2 OCO
1-phenyl- 79-81 cyclopropyl 446 HCOCH.sub.3 CH.sub.2 OCO 1-(4-chloro-
102-103 phenyl)-cyclopropyl 447 HCOCH.sub.3 CH.sub.2 OCO 1-Indanyl-
oil 5.15(S, 2H); 7.55(S, 1H) 448 HCOCH.sub.3 CH.sub.2
OCO 4-phenyl-phenyl 132 449 HCOCH.sub.3 CH.sub.2 OCO 4-phenyl-benzyl
oil 5.15(S, 2H); .55(S, 1H) 450 HCOCH.sub.3 CH.sub.2 OCO 2-phenyl-phenyl
85-87 451 HCOCH.sub.3 CH.sub.2 OCO 2-phenoxyphenyl oil 5.3(S, 2H);
7.55(S, 1H) 452 HCOCH.sub.3 CH.sub.2 OCO 2-naphthyl oil 5.45(S, 2H);
7.6(S, 1H) 453 HCOCH.sub.3 CH.sub.2 OCO 2-naphthylmethyl oil 5.15(S,
2H); 7.5(S, 1H) 454 HCOCH.sub.3 CH.sub.2 OCO 1-naphthyl 123-124 455
HCOCH.sub.3 CH.sub.2 OCO 1-naphthylmethyl oil 5.15(S, 2H); 7.55(S, 1H)
456 HCOCH.sub.3 CH.sub.2 OCO 3-phenoxyphenyl oil 5.35(S, 2H); 7.55(S,
1H) 457 HCOCH.sub.3 CH.sub.2 OCO n-heptodecyl 38-40 458 HCOCH.sub.3
CH.sub.2 OCO n-heptyl oil 5.1(S, 2H); 7.55(S, 1H) 459 HCOCH.sub.3
CH.sub.2 OCO t-butyl oil 5.1(S, 2H); 7.55(S, 1H) 460 HCOCH.sub.3
CH.sub.2 OCO iso-butyl oil 5.1(S, 2H); 7.55(S, 1H) 461 HCOCH.sub.3
CH.sub.2 OCO n-butyl oil 5.1(S, 2H); 7.55(S, 1H) 462 HCOCH.sub.3
CH.sub.2 OCO n-Propyl oil 5.1(S, 2H); 7.55(S, 1H) 463 HCOCH.sub.3
CH.sub.2 OCO Ethyl oil 5.1(S, 2H); 7.55(S, 1H) 464 HCOCH.sub.3 CH.sub.2 C
OOCH.sub.2 phenyl oil 5.15(S, 2H); 7.6(S, 1H) 465 HCOCH.sub.3 CH.sub.2
OCO(CH.sub.2).sub.2 phenyl oil 5.1(S, 2H); 7.55(S, 1H) 466 HCOCH.sub.3
CH.sub.2 OCO(CH.sub.2).sub.3 phenyl oil 5.15(S, 2H); 7.55(S, 1H) 467
HCOCH.sub.3 CH.sub.2 OCO 1-methylcyclo- 45-47 propyl 468 HCOCH.sub.3
CH.sub.2 OCO n-pentyl oil 5.1(S, 2H); 7.55(S, 1H) 469 HCOCH.sub.3
CH.sub.2 OCO n-hexyl oil 5.1(S, 2H); 7.55(S, 1H) 470 HCOCH.sub.3
CH.sub.2 OCO n-nonyl oil 5.1(S, 2H); 7.55(S, 1H) 471 HCOCH.sub.3
CH.sub.2 OCO n-undecyl oil 5.1(S, 2H); 7.55(S, 1H) 472 HCOCH.sub.3
CH.sub.2
S n-octyl oil 3.7(S, 2H); 7.55(S, 1H) 473 HCOCH.sub.3 O(CH.sub.2).sub.2
phenyl oil 4.2(t, J=7Hz.2H); 7.55(S, 1H) 474 HCOCH.sub.3 O(CH.sub.2).sub.
3 phenyl oil 3.95(t, J=7Hz, 2H); 7.55(S, 1H) 475 HCOCH.sub.3 CH.sub.2 O
2-naphthyl 164-165 476 HCOCH.sub.3 OCH.sub.2 2-naphthyl 74-75 477
HCOCH.sub.3 O(CH.sub.2).sub.2 CH.sub.3 oil 3.9(t, J=8Hz, 2H); 7.55(S,
1H) 478 HCOCH.sub.3 O(CH.sub.2).sub.3 CH.sub.3 oil 3.95(t, J=8Hz, 2H);
7.55(S, 1H) 479 HCOCH.sub.3 O(CH.sub.2).sub.5 CH.sub.3 oil 3.95(t,
J=7Hz, 2H); 7.55(S, 1H) 480 HCOCH.sub.3 O(CH.sub.2).sub.7 CH.sub.3 38-39
481 HCOCH.sub.3 O(CH.sub.2).sub.9 CH.sub.3 53-54 482 HCOCH.sub.3
O(CH.sub.2).sub.19 CH.sub.3 62-63 483 HCOCH.sub.3 OCH.sub.2 2,6-dimethylh
eptyl oil 4.0(m, 2H); 7.55(S, 1H) 484 HCOCH.sub.3 OCH.sub.2 2,6-dimethyl-
oil 4.0(m, 2H); 7.55(S, 1H) heptenyl-(5) 485 HCOCH.sub.3 OCH.sub.2
(trans)-2,6- oil 4.5(d, J=7Hz, 2H); 7.55(S, 1H) dimethyl-heptadienyl-(
1,5) 486 HCOCH.sub.3 OCH.sub.2 (cis)-2,6- oil 4.5(d, J=7Hz, 2H); 7.55(S,
1H) dimethyl-heptadienyl-(1,5) 487 HCOCH.sub.3 OCH.sub.2 (trans,
trans)- oil 4.5(d, J=7Hz, 2H); 7.55(S, 1H) (isomer mixture) 2,6,10-tri-
methylundecatrienyl-(1,5,9) 488 HCOCH.sub.3 OCH.sub.2 (trans)-1,5,9,1
3- oil 4.5(d, J=7Hz, 2H); 7.55(S, 1H) (isomer mixture) tetramethylpenta
decen-(1) 489 HCOCH.sub.3 OCH.sub.2 1-[2-methyl-3- oil 3.75(d, J=7Hz,
2H); 7.55(S, 1H) (4-fluorophenyl]-propenyl 490 O CH.sub.2
O 2-methylphenyl oil 5.1(s, 2H) 491 O CH.sub.2 O 3-methylphenyl 492 O
CH.sub.2 O 4-methylphenyl 493 O CH.sub.2 O 2,3-dimethylphenyl 494 O
CH.sub.2 O 2,4-dimethylphenyl 495 O CH.sub.2 O 2,5-dimethylphenyl 496 O
CH.sub.2 O 2,6-dimethylphenyl 497 O CH.sub.2 O 3,4-dimethylphenyl 498 O
CH.sub.2
O 3,5-dimethylphenyl
__________________________________________________________________________
##STR30##
No.
U A B mp NMR: δ(ppm)
__________________________________________________________________________
1 HCOCH.sub.3
CH.sub.2 CH.sub.2
H
2 HCOCH.sub.3
CH.sub.2 CH.sub.2
CH.sub.3
3 HCOCH.sub.3
›EXAMPLE 19 · 5 of 5
CH.sub.2 CH.sub.2
cyclohexyl
4 HCOCH.sub.3
CH.sub.2 CH.sub.2
phenyl
5 HCOCH.sub.3
CH.sub.2 CH.sub.2
2-pyridyl
6 HCOCH.sub.3
›CHCH H
7 HCOCH.sub.3
CHCH CH.sub.3
8 HCOCH.sub.3
CHCH cyclohexyl
9 HCOCH.sub.3
CHCH 2-naphthyl
10
HCOCH.sub.3
CHCH 2-pyridyl
11
HCOCH.sub.3
OCH.sub.2 H
12
HCOCH.sub.3
OCH.sub.2 CH.sub.3
13
HCOCH.sub.3
OCH.sub.2 cyclohexyl
14
HCOCH.sub.3
OCH.sub.2 phenyl 77-79
15
HCOCH.sub.3
OCH.sub.2 2-pyridyl
16
HCOCH.sub.3
OCH.sub.2 CO
H
17
HCOCH.sub.3
OCH.sub.2 CO
CH.sub. 3
18
HCOCH.sub.3
OCH.sub.2 CO
cyclohexyl
19
HCOCH.sub.3
OCH.sub.2 CO
phenyl
20
HCOCH.sub.3
OCH.sub.2 CO
2-pyridyl
21
HCOCH.sub.3
CH.sub.2 OCO
H oil 5.2(S, 2H); 7.6(S, 1H)
22
HCOCH.sub.3
CH.sub.2 OCO
CH.sub.3
69-70
23
HCOCH.sub.3
CH.sub.2 OCO
cyclohexyl
24
HCOCH.sub.3
CH.sub.2 OCO
phenyl 74-75
25
HCOCH.sub.3
CH.sub.2 OCO
2-pyridyl
26
HCOCH.sub.3
COOCH.sub.2 H 81-84
27
HCOCH.sub.3
COOCH.sub.2 CH.sub.3
28
HCOCH.sub.3
COOCH.sub.2 cyclohexyl
29
HCOCH.sub.3
COOCH.sub.2 phenyl
30
HCOCH.sub.3
COOCH.sub.2 2-pyridyl
31
HCOCH.sub.3
OCOCH.sub.2 H
32
HCOCH.sub.3
OCOCH.sub.2 CH.sub.3
33
HCOCH.sub.3
OCOCH.sub.2 cyclohexyl
34
HCOCH.sub.3
OCOCH.sub.2 phenyl
35
HCOCH.sub.3
OCOCH.sub.2 2-pyridyl
36
HCOCH.sub.3
OCO phenyl
37
HCOCH.sub.3
OCH.sub.2 COO
CH.sub.3
38
HCOCH.sub.3
O(CH.sub.2).sub.3 COO
CH.sub.3
57-58
39
HCOCH.sub.3
O(CH.sub.2).sub.7 COO
CH.sub.3
44
40
HCOCH.sub.3
O(CH.sub.2).sub.2 O
H
41
HCOCH.sub.3
O(CH.sub.2).sub.2 O
CH.sub.3
42
HCOCH.sub.3
O(CH.sub.2).sub.2 O
cyclohexyl
43
HCOCH.sub.3
O(CH.sub.2).sub.2 O
phenyl
44
HCOCH.sub.3
O(CH.sub.2).sub.2 O
2-pyridyl
45
HCOCH.sub.3
O(CH.sub.2).sub.3 O
H
46
HCOCH.sub.3
O(CH.sub.2).sub.3 O
CH.sub.3
47
HCOCH.sub.3
O(CH.sub.2).sub.3 O
cyclohexyl
47
HCOCH.sub.3
O(CH.sub.2).sub.3 O
cyclohexyl
48
HCOCH.sub.3
O(CH.sub.2).sub.3 O
phenyl
49
HCOCH.sub.3
O(CH.sub.2).sub.3 O
2-pyridyl
50
HCOCH.sub.3
O(CH.sub.2).sub.4 O
H
51
HCOCH.sub.3
O(CH.sub.2).sub.4 O
CH.sub.3
52
HCOCH.sub.3
O(CH.sub.2).sub. 4 O
cycloheyl
53
HCOCH.sub.3
O(CH.sub.2).sub.4 O
phenyl
54
HCOCH.sub.3
O(CH.sub.2).sub.4 O
2-pyridyl
55
HCOCH.sub.3
O(CH.sub.2).sub.5 O
H
56
HCOCH.sub.3
O(CH.sub.2).sub.5 O
CH.sub.3
57
HCOCH.sub.3
O(CH.sub.2).sub.5 O
cyclohexyl
58
HCOCH.sub.3
O(CH.sub.2).sub.5 O
phenyl
59
HCOCH.sub.3
O(CH.sub.2).sub.5 O
2-pyridyl
60
HCOCH.sub.3
O(CH.sub.2).sub.6 O
H
61
HCOCH.sub.3
O(CH.sub.2).sub.6 O
CH.sub.3
62
HCOCH.sub.3
O(CH.sub.2).sub.6 O
cyclohexyl
63
HCOCH.sub.3
O(CH.sub.2).sub.6 O
phenyl
64
HCOCH.sub.3
O(CH.sub.2).sub.6 O
2-pyridyl
65
HCOCH.sub.3
O(CH.sub.2).sub.8 O
H
66
HCOCH.sub.3
O(CH.sub.2).sub.8 O
CH.sub.3
67
HCOCH.sub.3
O(CH.sub.2).sub.8 O
cyclohexyl
68
HCOCH.sub.3
O(CH.sub.2).sub.8 O
phenyl
69
HCOCH.sub.3
O(CH.sub.2).sub.8 O
2-pyridyl
70
HCOCH.sub.3
O(CH.sub.2).sub.10 O
H
71
HCOCH.sub.3
O(CH.sub.2).sub.10 O
CH.sub.3
72
HCOCH.sub.3
O(CH.sub.2).sub.10 O
cyclohexyl
73
HCOCH.sub.3
O(CH.sub.2).sub.10 O
phenyl
74
HCOCH.sub.3
O(CH.sub.2).sub.10 O
2-pyridyl
75
HCOCH.sub.3
O phenyl 99-100
76
HCOCH.sub.3
CH.sub.2 O CH.sub.3
77
HCOCH.sub.3
CH.sub.2 O cyclohexyl
78
HCOCH.sub.3
CH.sub.2 O phenyl
79
HCOCH.sub.3
CH.sub.2 O pyridyl
80
HCOCH.sub.3
CH.sub.2 SCH.sub.2
H
81
HCOCH.sub.3
CH.sub.2 SCH.sub.2
CH.sub.3
82
HCOCH.sub.3
CH.sub.2 SCH.sub.2
cyclohexyl
83
HCOCH.sub.3
CH.sub.2 SCH.sub.2
phenyl
84
HCOCH.sub.3
CH.sub.2 SCH.sub.2
2-pyridyl
85
HCOCH.sub.3
CH.sub.2 N(CH.sub.3)
H
86
HCOCH.sub.3
CH.sub.2 N(CH.sub.3)
CH.sub.3
87
HCOCH.sub. 3
CH.sub.2 N(CH.sub.3)
cyclohexyl
88
HCOCH.sub.3
CH.sub.2 N(CH.sub.3)
phenyl
89
HCOCH.sub.3
CH.sub.2 N(CH.sub.3)
2-pyridyl
90
HCOCH.sub.3
CH(CN)OCOCH.sub.2
H
91
HCOCH.sub.3
CH(CN)OCOCH.sub.2
CH.sub.3
92
HCOCH.sub.3
CH(CN)OCOCH.sub.2
cyclohexyl
93
HCOCH.sub.3
CH(CN)OCOCH.sub.2
phenyl
94
HCOCH.sub.3
CH(CN)OCOCH.sub.2
pyridyl
95
HCOCH.sub.3
CH(CN)OCO phenyl
96
HCOCH.sub.3
›CHN H
97
HCOCH.sub.3
CHN CH.sub.3
98
HCOCH.sub.3
CHN cyclohexyl
99
HCOCH.sub.3
CHN phenyl
100
HCOCH.sub.3
CHN 2-pyridyl
101
HCOCH.sub.3
CHNOCH.sub.2
H
102
HCOCH.sub.3
CHNOCH.sub.2
CH.sub.3
103
HCOCH.sub.3
CHNOCH.sub.2
cyclohexyl
104
HCOCH.sub.3
CHNOCH.sub.2
phenyl
105
HCOCH.sub.3
CHNOCH.sub.2
2-pyridyl
106
NOCH.sub.3
CH.sub.2 CH.sub.2
H
107
NOCH.sub.3
CH.sub.2 CH.sub.2
CH.sub.3
108
NOCH.sub.3
CH.sub.2 CH.sub.2
cyclohexyl
109
NOCH.sub.3
CH.sub.2 CH.sub.2
phenyl
110
NOCH.sub.3
CH.sub.2 CH.sub.2
2-pyridyl
111
NOCH.sub.3
›CHCH H
112
NOCH.sub.3
CHCH CH.sub.3
113
NOCH.sub.3
CHCH cyclohexyl
114
NOCH.sub.3
CHCH phenyl
115
NOCH.sub.3
CHCH 2-pyridyl
116
NOCH.sub.3
OCH.sub.2 H
117
NOCH.sub.3
OCH.sub.2 CH.sub.3
118
NOCH.sub.3
OCH.sub.2 cyclohexyl
119
NOCH.sub.3
OCH.sub.2 phenyl
120
NOCH.sub.3
OCH.sub.2 2-pyridyl
121
NOCH.sub.3
OCH.sub.2 CO
H
122
NOCH.sub.3
OCH.sub.2 CO
CH.sub.3
123
NOCH.sub.3
OCH.sub.2 CO
cyclohexyl
124
NOCH.sub.3
OCH.sub.2 CO
phenyl
125
NOCH.sub.3
OCH.sub.2 CO
2-pyridyl
126
NOCH.sub.3
CH.sub.2 OCO
H
127
NOCH.sub.3
CH.sub.2 OCO
CH.sub.3
128
NOCH.sub.3
CH.sub.2 OCO
cyclohexyl
129
NOCH.sub.3
CH.sub.2 OCO
phenyl
130
NOCH.sub.3
CH.sub.2 OCO
2-pyridyl
131
NOCH.sub.3
COOCH.sub.2 H
132
NOCH.sub.3
COOCH.sub.2 CH.sub.3
133
NOCH.sub.3
COOCH.sub.2 cyclohexyl
134
NOCH.sub.3
COOCH.sub.2 phenyl
135
NOCH.sub.3
COOCH.sub.2 2-pyridyl
136
NOCH.sub.3
OCOCH.sub.2 H
137
NOCH.sub.3
OCOCH.sub.2 CH.sub.3
138
NOCH.sub.3
OCOCH.sub.2 cyclohexyl
139
NOCH.sub.3
OCOCH.sub.2 phenyl
140
NOCH.sub.3
OCOCH.sub.2 2-pyridyl
141
NOCH.sub.3
OCO phenyl
142
NOCH.sub.3
OCH.sub.2 COO
CH.sub.3
143
NOCH.sub.3
O(CH.sub.2).sub.3 COO
CH.sub.3
144
NOCH.sub.3
O(CH.sub.2).sub.7 COO
CH.sub.3
145
NOCH.sub.3
O(CH.sub.2).sub.2 O
H
146
NOCH.sub.3
O(CH.sub.2).sub.2 O
CH.sub.3
147
NOCH.sub.3
O(CH.sub.2).sub.2 O
cyclohexyl
148
NOCH.sub.3
O(CH.sub.2).sub.2 O
phenyl
149
NOCH.sub.3
O(CH.sub.2).sub.2 O
2-pyridyl
150
NOCH.sub.3
O(CH.sub.2).sub.3 O
H
151
NOCH.sub.3
O(CH.sub.2).sub.3 O
CH.sub.3
152
NOCH.sub.3
O(CH.sub.2).sub.3 O
cyclohexyl
153
NOCH.sub.3
O(CH.sub.2).sub.3 O
phenyl
154
NOCH.sub. 3
O(CH.sub.2).sub.3 O
2-pyridyl
155
NOCH.sub.3
O(CH.sub.2).sub.4 O
H
156
NOCH.sub.3
O(CH.sub.2).sub.4 O
CH.sub.3
157
NOCH.sub.3
O(CH.sub.2).sub.4 O
cyclohexyl
158
NOCH.sub.3
O(CH.sub.2).sub.4 O
phenyl
159
NOCH.sub.3
O(CH.sub.2).sub.4 O
2-pyridyl
160
NOCH.sub.3
O(CH.sub.2).sub.5 O
H
161
NOCH.sub.3
O(CH.sub.2).sub.5 O
CH.sub.3
162
NOCH.sub.3
O(CH.sub.2).sub.5 O
cyclohexyl
163
NOCH.sub.3
O(CH.sub.2).sub.5 O
phenyl
164
NOCH.sub.3
O(CH.sub.2).sub.5 O
2-pyridyl
165
NOCH.sub.3
O(CH.sub.2).sub.6 O
H
166
NOCH.sub.3
O(CH.sub.2).sub.6 O
CH.sub.3
167
NOCH.sub.3
O(CH.sub.2).sub.6 O
cyclohexyl
168
NOCH.sub.3
O(CH.sub.2).sub.6 O
phenyl
169
NOCH.sub.3
O(CH.sub.2).sub.6 O
2-pyridyl
170
NOCH.sub.3
O(CH.sub.2).sub.8 O
H
171
NOCH.sub.3
O(CH.sub.2).sub.8 O
CH.sub.3
172
NOCH.sub.3
O(CH.sub.2).sub.8 O
cyclohexyl
173
NOCH.sub.3
O(CH.sub.2).sub.8 O
phenyl
174
NOCH.sub.3
O(CH.sub.2).sub.8 O
2-pyridyl
175
NOCH.sub.3
O(CH.sub.2).sub.10 O
H
176
NOCH.sub.3
O(CH.sub.2).sub.10 O
CH.sub.3
177
NOCH.sub.3
O(CH.sub.2).sub.10 O
cyclohexyl
178
NOCH.sub.3
O(CH.sub.2).sub.10 O
phenyl
179
NOCH.sub.3
O(CH.sub.2).sub.10 O
2-pyridyl
180
NOCH.sub.3
CH.sub.2 O H
181
NOCH.sub.3
CH.sub.2 O CH.sub.3
182
NOCH.sub.3
CH.sub.2 O cyclohexyl
183
NOCH.sub.3
CH.sub.2 O phenyl
184
NOCH.sub.3
CH.sub.2 O pyridyl
185
NOCH.sub.3
CH.sub.2 SCH.sub.2
H
186
NOCH.sub.3
CH.sub.2 SCH.sub.2
CH.sub.3
187
NOCH.sub.3
CH.sub.2 SCH.sub.2
cyclohexyl
188
NOCH.sub.3
CH.sub.2 SCH.sub.2
phenyl
189
NOCH.sub.3
CH.sub.2 SCH.sub.2
2-pyridyl
190
NOCH.sub.3
CH.sub.2 N(CH.sub.3)
H
191
NOCH.sub.3
CH.sub. 2 N(CH.sub.3)
CH.sub.3
192
NOCH.sub.3
CH.sub.2 N(CH.sub.3)
cyclohexyl
193
NOCH.sub.3
CH.sub.2 N(CH.sub.3)
phenyl
194
NOCH.sub.3
CH.sub.2 N(CH.sub.3)
2-pyridyl
195
NOCH.sub.3
CH(CN)OCOCH.sub.2
H
196
NOCH.sub.3
CH(CN)OCOCH.sub.2
CH.sub.3
197
NOCH.sub.3
CH(CN)OCOCH.sub.2
cyclohexyl
198
NOCH.sub.3
CH(CN)OCOCH.sub.2
phenyl
199
NOCH.sub.3
CH(CN)OCOCH.sub.2
pyridyl
200
NOCH.sub.3
CH(CN)OCO phenyl
201
NOCH.sub.3
›CHN H
202
NOCH.sub.3
CHN CH.sub.3
203
NOCH.sub.3
CHN cyclohexyl
204
NOCH.sub.3
CHN phenyl
205
NOCH.sub.3
CHN 2-pyridyl
206
NOCH.sub.3
CHNOCH.sub.2
H
207
NOCH.sub.3
CHNOCH.sub.2
CH.sub.3
208
NOCH.sub.3
CHNOCH.sub.2
cyclohexyl
209
NOCH.sub.3
CHNOCH.sub.2
phenyl
210
NOCH.sub.3
CHNOCH.sub.2
2-pyridyl
211
HCCH.sub.3
CH.sub.2 CH.sub.2
H
212
HCCH.sub.3
CH.sub.2 CH.sub.2
CH.sub.3
213
HCCH.sub.3
CH.sub.2 CH.sub.2
cyclohexyl
214
HCCH.sub. 3
CH.sub.2 CH.sub.2
phenyl
215
HCCH.sub.3
CH.sub.2 CH.sub.2
2-pyridyl
216
HCCH.sub.3
›CHCH H
217
HCCH.sub.3
CHCH CH.sub.3
218
HCCH.sub.3
CHCH cyclohexyl
219
HCCH.sub.3
CHCH phenyl
220
HCCH.sub.3
CHCH 2-pyridyl
221
HCCH.sub.3
OCH.sub.2 H
222
HCCH.sub.3
OCH.sub.2 CH.sub.3
223
HCCH.sub.3
OCH.sub.2 cyclohexyl
224
HCCH.sub.3
OCH.sub.2 phenyl
225
HCCH.sub.3
OCH.sub.2 2-pyridyl
226
HCCH.sub.3
OCH.sub.2 CO
H
227
HCCH.sub.3
OCH.sub.2 CO
CH.sub.3
228
HCCH.sub.3
OCH.sub.2 CO
cyclohexyl
229
HCCH.sub.3
OCH.sub.2 CO
phenyl
230
HCCH.sub.3
OCH.sub.2 CO
2-pyridyl
231
HCCH.sub.3
CH.sub.2 OCO
H
232
HCCH.sub.3
CH.sub.2 OCO
CH.sub.3
233
HCCH.sub.3
CH.sub.2 OCO
cyclohexyl
234
HCCH.sub.3
CH.sub.2 OCO
phenyl
235
HCCH.sub.3
CH.sub.2 OCO
2-pyridyl
236
HCCH.sub.3
COOCH.sub.2 H
237
HCCH.sub.3
COOCH.sub.2 CH.sub.3
238
HCCH.sub.3
COOCH.sub.2 cyclohexyl
239
HCCH.sub.3
COOCH.sub.2 phenyl
240
HCCH.sub.3
COOCH.sub.2 2-pyridyl
241
HCCH.sub.3
OCOCH.sub.2 H
242
HCCH.sub.3
OCOCH.sub.2 CH.sub.3
243
HCCH.sub.3
OCOCH.sub.2 cyclohexyl
244
HCCH.sub.3
OCOCH.sub.2 phenyl
245
HCCH.sub.3
OCOCH.sub.2 2-pyridyl
246
HCCH.sub.3
OCO phenyl
247
HCCH.sub.3
OCH.sub.2 COO
CH.sub.3
248
HCCH.sub.3
O(CH.sub.2).sub.3 COO
CH.sub.3
249
HCCH.sub.3
O(CH.sub.2).sub.7 COO
CH.sub.3
250
HCCH.sub.3
O(CH.sub.2).sub.2 O
H
251
HCCH.sub.3
O(CH.sub.2).sub.2 O
CH.sub.3
252
HCCH.sub.3
O(CH.sub.2).sub.2 O
cyclohexyl
253
HCCH.sub.3
O(CH.sub.2).sub.2 O
phenyl
254
HCCH.sub.3
O(CH.sub.2).sub.2 O
2-pyridyl
255
HCCH.sub.3
O(CH.sub.2).sub.3 O
H
256
HCCH.sub.3
O(CH.sub.2).sub.3 O
CH.sub.3
257
HCCH.sub.3
O(CH.sub.2).sub.3 O
cyclohexyl
258
HCCH.sub.3
O(CH.sub.2).sub.3 O
phenyl
259
HCCH.sub.3
O(CH.sub.2).sub.3 O
2-pryidyl
260
HCCH.sub.3
O(CH.sub.2).sub.4 O
H
261
HCCH.sub.3
O(CH.sub.2).sub.4 O
CH.sub.3
262
HCCH.sub.3
O(CH.sub.2).sub.4 O
cyclohexyl
263
HCCH.sub.3
O(CH.sub.2).sub.4 O
phenyl
264
HCCH.sub.3
O(CH.sub.2).sub.4 O
2-pyridyl
265
HCCH.sub.3
O(CH.sub.2).sub.5 O
H
266
HCCH.sub.3
O(CH.sub.2).sub.5 O
CH.sub.3
267
HCCH.sub.3
O(CH.sub.2).sub.5 O
cyclohexyl
268
HCCH.sub.3
O(CH.sub.2).sub.5 O
phenyl
269
HCCH.sub.3
O(CH.sub.2).sub.5 O
2-pyridyl
270
HCCH.sub.3
O(CH.sub.2).sub.6 O
H
271
HCCH.sub.3
O(CH.sub.2).sub.6 O
CH.sub.3
272
HCCH.sub. 3
O(CH.sub.2).sub.6 O
cyclohexyl
273
HCCH.sub.3
O(CH.sub.2).sub.6 O
phenyl
274
HCCH.sub.3
O(CH.sub.2).sub.6 O
2-pyridyl
275
HCCH.sub.3
O(CH.sub.2).sub.8 O
H
276
HCCH.sub.3
O(CH.sub.2).sub.8 O
CH.sub.3
277
HCCH.sub.3
O(CH.sub.2).sub.8 O
cyclohexyl
278
HCCH.sub.3
O(CH.sub.2).sub.8 O
phenyl
279
HCCH.sub.3
O(CH.sub.2).sub.8 O
2-pyridyl
280
HCCH.sub.3
O(CH.sub.2).sub.10 O
H
281
HCCH.sub.3
O(CH.sub.2).sub.10 O
CH.sub.3
282
HCCH.sub.3
O(CH.sub.2).sub.10 O
cyclohexyl
283
HCCH.sub.3
O(CH.sub.2).sub.10 O
phenyl
284
HCCH.sub.3
O(CH.sub.2).sub.10 O
2-pyridyl
285
HCCH.sub.3
CH.sub.2 O H
286
HCCH.sub.3
CH.sub.2 O CH.sub.3
287
HCCH.sub.3
CH.sub.2 O cyclohexyl
288
HCCH.sub.3
CH.sub.2 O phenyl
289
HCCH.sub.3
CH.sub.2 O pyridyl
290
HCCH.sub.3
CH.sub.2 SCH.sub.2
H
291
HCCH.sub.3
CH.sub.2 SCH.sub.2
CH.sub.3
292
HCCH.sub.3
CH.sub.2 SCH.sub.2
cyclohexyl
293
HCCH.sub.3
CH.sub.2 SCH.sub.2
phenyl
294
HCCH.sub.3
CH.sub.2 SCH.sub.2
2-pyridyl
295
HCCH.sub.3
CH.sub.2 N(CH.sub.3)
H
296
HCCH.sub.3
CH.sub.2 N(CH.sub.3)
CH.sub.3
297
HCCH.sub.3
CH.sub.2 N(CH.sub.3)
cyclohexyl
298
HCCH.sub.3
CH.sub.2 N(CH.sub.3)
phenyl
299
HCCH.sub.3
CH.sub.2 N(CH.sub.3)
2-pyridyl
300
HCCH.sub.3
CH(CN)OCOCH.sub.2
H
301
HCCH.sub.3
CH(CN)OCOCH.sub.2
CH.sub.3
302
HCCH.sub.3
CH(CN)OCOCH.sub.2
cyclohexyl
303
HCCH.sub.3
CH(CN)OCOCH.sub.2
phenyl
304
HCCH.sub.3
CH(CN)OCOCH.sub.2
pyridyl
305
HCCH.sub.3
CH(CN)OCO phenyl
306
HCCH.sub.3
›CHN H
307
HCCH.sub.3
CHN CH.sub.3
308
HCCH.sub.3
CHN cyclohexyl
309
HCCH.sub.3
CHN phenyl
310
HCCH.sub.3
CHN 2-pyridyl
311
HCCH.sub.3
CHNOCH.sub.2
H
312
HCCH.sub.3
CHNOCH.sub.2
CH.sub.3
313
HCCH.sub.3
CHNOCH.sub.2
cyclohexyl
314
HCCH.sub.3
CHNOCH.sub.2
phenyl
315
HCCH.sub.3
CHNOCH.sub.2
2-pyridyl
316
O CH.sub.2 CH.sub.2
H
317
O CH.sub.2 CH.sub.2
CH.sub.3
318
O CH.sub.2 CH.sub.2
cyclohexyl
319
O CH.sub.2 CH.sub.2
phenyl
320
O CH.sub.2 CH.sub.2
2-pyridyl
312
›O CHCH H
322
O CHCH CH.sub.3
323
O CHCH cyclohexyl
324
O CHCH phenyl
325
O CHCH 2-pyridyl
326
O OCH.sub.2 H
327
O OCH.sub.2 CH.sub.3
328
O OCH.sub.2 cyclohexyl
329
O OCH.sub.2 phenyl
330
O OCH.sub.2 2-pyridyl
331
O CH.sub.2 O H
332
O CH.sub.2 O CH.sub.3
333
O CH.sub.2 O cyclohexyl
334
O CH.sub.2 O phenyl
335
O CH.sub.2 O 2-pyridyl
336
O CH.sub. 2 OCO
H
337
O CH.sub.2 OCO
CH.sub.3
338
O CH.sub.2 OCO
cyclohexyl
339
O CH.sub.2 OCO
phenyl
340
O CH.sub.2 OCO
2-pyridyl
341
NNHCH.sub.3
CH.sub.2 CH.sub.2
H
342
NNHCH.sub.3
CH.sub.2 CH.sub.2
CH.sub.3
343
NNHCH.sub.3
CH.sub.2 CH.sub.2
cyclohexyl
344
NNHCH.sub.3
CH.sub.2 CH.sub.2
phenyl
345
NNHCH.sub.3
CH.sub.2 CH.sub.2
2-pyridyl
346
NNHCH.sub.3
›CHCH H
347
NNHCH.sub.3
CHCH CH.sub.3
348
NNHCH.sub.3
CHCH cyclohexyl
349
NNHCH.sub.3
CHCH phenyl
350
NNHCH.sub.3
CHCH 2-pyridyl
351
NNHCH.sub.3
OCH.sub.2 H
352
NNHCH.sub.3
OCH.sub.2 CH.sub.3
353
NNHCH.sub.3
OCH.sub.2 cyclohexyl
354
NNHCH.sub.3
OCH.sub.2 phenyl
355
NNHCH.sub.3
OCH.sub.2 2-pyridyl
356
NNHCH.sub.3
CH.sub.2 O H
357
NNHCH.sub.3
CH.sub.2 O CH.sub.3
358
NNHCH.sub.3
CH.sub.2 O cyclohexyl
359
NNHCH.sub.3
CH.sub.2 O phenyl
360
NNHCH.sub.3
CH.sub.2 O 2-pyridyl
361
NNHCH.sub.3
CH.sub.2 OCO
H
362
NNHCH.sub.3
CH.sub.2 OCO
CH.sub.3
363
NNHCH.sub.3
CH.sub.2 OCO
cyclohexyl
364
NNHCH.sub.3
CH.sub.2 OCO
phenyl
365
NNHCH.sub.3
CH.sub.2 OCO
2-pyridyl
366
CH.sub.2 CH.sub.2 CH.sub.2
H
367
CH.sub.2 CH.sub.2 CH.sub.2
CH.sub.3
368
CH.sub.2 CH.sub.2 CH.sub.2
cyclohexyl
369
CH.sub.2 CH.sub.2 CH.sub.2
phenyl
370
CH.sub.2 CH.sub.2 CH.sub.2
2-pyridyl
371
CH.sub.2 CHCH H
372
CH.sub.2 CHCH CH.sub.3
373
CH.sub.2 CHCH cyclohexyl
374
CH.sub.2 CHCH phenyl
375
CH.sub.2 CHCH 2-pyridyl
376
CH.sub.2 OCH.sub.2 H
377
CH.sub.2 OCH.sub.2 CH.sub.3
378
CH.sub.2 OCH.sub.2 cyclohexyl
379
CH.sub.2 OCH.sub.2 phenyl
380
CH.sub.2 OCH.sub.2 2-pyridyl
381
CH.sub.2 CH.sub.2 O H
382
CH.sub.2 CH.sub.2 O CH.sub.3
383
CH.sub.2 CH.sub.2 O cyclohexyl
384
CH.sub.2 CH.sub.2 O phenyl
385
CH.sub.2 CH.sub.2 O 2-pyridyl
386
CH.sub.2 CH.sub.2 OCO
H
387
CH.sub.2 CH.sub.2 OCO
CH.sub.3
388
CH.sub.2 CH.sub.2 OCO
cyclohexyl
389
CH.sub.2 CH.sub.2 OCO
phenyl
390
CH.sub.2 CH.sub.2 OCO
2-pyridyl
391
CHCH.sub.2 CH.sub.3
CH.sub.2 CH.sub.2
H
392
CHCH.sub.2 CH.sub.3
CH.sub.2 CH.sub.2
CH.sub.3
393
CHCH.sub.2 CH.sub.3
CH.sub.2 CH.sub.2
cyclohexyl
394
CHCH.sub.2 CH.sub.3
CH.sub.2 CH.sub.2
phenyl
395
CHCH.sub.2 CH.sub.3
CH.sub.2 CH.sub.2
2-pyridyl
396
CHCH.sub.2 CH.sub.3
›CHCH H
397
CHCH.sub.2 CH.sub.3
CHCH CH.sub.3
398
CHCH.sub.2 CH.sub.3
CHCH cyclohexyl
399
CHCH.sub.2 CH.sub.3
CHCH phenyl
400
CHCH.sub.2 CH.sub.3
CHCH 2-pyridyl
401
CHCH.sub.2 CH.sub.3
OCH.sub.2 H
402
CHCH.sub.2 CH.sub.3
OCH.sub. 2 CH.sub.3
403
CHCH.sub.2 CH.sub.3
OCH.sub.2 cyclohexyl
404
CHCH.sub.2 CH.sub.3
OCH.sub.2 phenyl
405
CHCH.sub.2 CH.sub.3
OCH.sub.2 2-pyridyl
406
CHCH.sub.2 CH.sub.3
CH.sub.2 O H
407
CHCH.sub.2 CH.sub.3
CH.sub.2 O CH.sub.3
408
CHCH.sub.2 CH.sub.3
CH.sub.2 O cyclohexyl
409
CHCH.sub.2 CH.sub.3
CH.sub.2 O phenyl
410
CHCH.sub.2 CH.sub.3
CH.sub.2 O 2-pyridyl
411
CHCH.sub.2 CH.sub.3
CH.sub.2 OCO
H
412
CHCH.sub.2 CH.sub.3
CH.sub.2 OCO
CH.sub.3
413
CHCH.sub.2 CH.sub.3
CH.sub.2 OCO
cyclohexyl
414
CHCH.sub.2 CH.sub.3
CH.sub.2 OCO
phenyl
415
CHCH.sub.2 CH.sub.3
CH.sub.2 OCO
2-pyridyl
416
CHSCH.sub.3
CH.sub.2 CH.sub.2
H
417
CHSCH.sub.3
CH.sub.2 CH.sub.2
CH.sub.3
418
CHSCH.sub.3
CH.sub.2 CH.sub.2
cyclohexyl
419
CHS CH.sub.3
CH.sub.2 CH.sub.2
phenyl
420
CHSCH.sub.3
CH.sub.2 CH.sub.2
2-pyridyl
421
CHSCH.sub.3
›CHCH H · 1 of 24
422
CHSCH.sub.3
CHCH CH.sub.3
423
CHSCH.sub.3
CHCH cyclohexyl
424
CHSCH.sub.3
CHCH phenyl
425
CHSCH.sub.3
CHCH 2-pyridyl
426
CHSCH.sub.3
OCH.sub.2 H
427
CHSCH.sub.3
OCH.sub.2 CH.sub.3
428
CHSCH.sub.3
OCH.sub.2 cyclohexyl
429
CHSCH.sub.3
OCH.sub.2 phenyl
430
CHSCH.sub.3
OCH.sub.2 2-pyridyl
431
CHSCH.sub.3
CH.sub.2 O H
432
CHSCH.sub.3
CH.sub.2 O CH.sub.3
433
CHSCH.sub.3
CH.sub.2 O cyclohexyl
434
CHSCH.sub.3
CH.sub.2 O phenyl
435
CHSCH.sub.3
CH.sub.2 O 2-pyridyl
436
CHSCH.sub.3
CH.sub.2 OCO
H
437
CHSCH.sub.3
CH.sub.2 OCO
CH.sub.3
438
CHSCH.sub.3
CH.sub.2 OCO
cyclohexyl
439
CHSCH.sub.3
CH.sub.2 O CO
phenyl
440
CHSCH.sub.3
CH.sub.2 OCO
2-pyridyl
441
HCOCH.sub.3
CH.sub.2 OCO
n-heptadecyl
37-38
442
HCOCH.sub.3
CH.sub.2 OCO
n-heptyl
oil 5.1(S, 2H); 7.55(S, 1H)
443
HCOCH.sub.3
CH.sub.2 OCO
t-butyl
oil 5.1(S, 2H); 7.6(S, 1H)
444
HCOCH.sub.3
CH.sub.2 OCO
iso-butyl
oil 5.1(S, 2H); 7.55(S, 1H)
445
HCOCH.sub.3
CH.sub.2 OCO
n-butyl
oil 5.1(S, 2H); 7.55(S, 1H)
446
HCOCH.sub.3
CH.sub.2 OCO
n-propyl
oil 5.1(S, 2H); 7.55(S, 1H)
447
HCOCH.sub.3
CH.sub.2 OCO
n-ethyl
oil 5.1(S, 2H); 7.55(S, 1H)
448
HCOCH.sub.3
CH.sub.2 OCOCH.sub.2
phenyl 59-60
449
HCOCH.sub.3
CH.sub.2 OCO(CH.sub.2).sub.2
phenyl oil 5.1(S, 2H); 7.55(S, 1H)
450
HCOCH.sub.3
CH.sub.2 OCO(CH.sub.2).sub.3
phenyl oil 5.1(S, 2H); 7.55(S, 1H)
451
HCOCH.sub.3
O(CH.sub.2).sub.2 O
A oil 4.1(t, J=5Hz, 2H); 7.55(S, 1H)
452
HCOCH.sub.3
O(CH.sub.2).sub.3 O
H oil 4.1(t, J=6Hz, 2H); 7.55(S, 1H)
453
HCOCH.sub.3
O(CH.sub.2).sub. 4 O
H oil 4.0(t, J=6Hz, 2H); 7.55(S, 1H)
454
HCOCH.sub.3
O(CH.sub.2).sub.8 O
H 54-55
__________________________________________________________________________
______________________________________
##STR31##
No. X.sub.m mp NMR: δ(ppm)
______________________________________
1 2-F oil 5.15(S, 2H);
7.55(S, 1H)
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl oil 5.15(S, 2H);
7.55(S, 1H)
9 3-Cl oil 5.05(S, 2H);
7.55(S, 1H)
10 4-Cl 64-67
11 2,3-Cl.sub.2 106-108
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
205 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-J
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3 78-79
66 3-CH.sub.3 88-90
67 4-CH.sub.3 116-118
68 2,3-(CH.sub.3).sub.2
69-71
69 2,4-(CH.sub.3).sub.2
79-82
70 2,5-(CH.sub.3).sub.2
82-84
71 2,6-(CH.sub.3).sub.2
59-61
72 3,4-(CH.sub.3).sub.2
83-84
73 3,5-(CH.sub.3).sub.2
76-77
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,3,6-(CH.sub.3).sub.3
79 2,3,4-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-SC.sub.4 H.sub.9
101 3-SC.sub.4 H.sub.9
102 4-SC.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub. 2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl)
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2 C.sub.6 H.sub.5
137 3-CH.sub.2 C.sub.6 H.sub.5
138 4-CH.sub.2 C.sub.6 H.sub.5
139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5 149-150
144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3 oil 5.15(S, 2H);
7.55(S, 1H)
159 3-OCH.sub.3 oil 5.05(S, 2H);
7.55(S, 1H)
200 4-OCH.sub.3 107-109
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
177 3-OCH.sub.2 C.sub.6 H.sub.5
178 4-OCH.sub.2 C.sub.6 H.sub.5
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3 oil 5.2(S, 2H);
7.55(S, 1H)
184 3-CF.sub.3
›CHCH H · 2 of 24
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.2, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3 oil 5.1(s, 2H);
7.6(s, 1H)
262 3-CHNOCH.sub.3 65-68
263 4-CHNOCH.sub.3 69-72
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(n-C.sub.6 H.sub. 13)
oil 5.1(s, 2H);
7.6(s, 1H)
274 3-CHNO(n-C.sub.6 H.sub.13)
oil 5.1(s, 2H);
7.6(s, 1H)
275 4-CHNO(n-C.sub.6 H.sub.13)
oil 5.1(s, 2H);
7.6(s, 1H)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
oil 5.1(s, 2H).
7.55(s, 1H)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
oil 5.1(s, 2H);
7.6(s, 1H)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
93-96
282 2-CO.sub.2 CH.sub.3
65-66
283 3-CO.sub.2 CH.sub.3
69-72
284 4-CO.sub.2 CH.sub.3
106-107
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (n-C.sub.6 H.sub.13)
295 3-CO.sub.2 (n-C.sub.6 H.sub.13)
296 4-CO.sub.2 (n-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2 CHCH.sub.2
oil 5.1(s, 2H);
7.6(s, 1H)
301 3-CHNOCH.sub.2 CHCH.sub.2
oil 5.1(s, 2H);
7.6(s, 1H)
302 4-CHNOCH.sub.2 CHCH.sub.2
oil 5.1(s, 2H);
7.6(s, 1H)
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.17)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO 95-96
331 3-CHO
332 4-CHO 123-125
333 2-CH.sub.3 -4-CHNO-allyl
oil 5.1(s, 2H);
7.55(s, 1H)
334 2-CH.sub.3 -5-CHNO-allyl
oil 5.1(s, 2H);
7.6(s, 1H)
335 2-CH.sub.3 -6-CHNO-allyl
oil 4.85(s, 2H);
7.6(s, 1H)
336 3-CH.sub.3 -6-CHNO-allyl
97-98
337 4-CH.sub.3 -6-CHNO-allyl
oil 5.05(s, 2H);
7.6(s, 1H)
______________________________________
______________________________________
##STR32##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9a) 3-Cl; oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.05(s, 2H)
9b 3-Cl; 82-85
polar isomer
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65a) 2-CH.sub.3 :non-polar
oil 3.95(S, 3H); 4.05(S, 3H);
isomer 5.05(S, 2H)
65b) 2-CH.sub.3 :polar isomer
99-100
66a) 3-CH.sub.3 :non-polar
oil 3.9(S, 3H); 4.0(S, 3H);
isomer 5.05(S, 2H)
66b) 3-CH.sub.3 :polar isomer
51-54
67a) 4-CH.sub.3 :non-polar
oil 3.9(S, 3H); 4.0(S, 3H);
isomer 5.0(S, 2H)
67b) 4-CH.sub.3 :polar isomer
102-103
68a) non-polar isomer;
oil 3.95(s, 3H); 4.05(s, 3H);
2,3-(CH.sub.3 ).sub.2 5.05(s, 2H)
›CHCH H · 3 of 24
68b) polar isomer; 86-89
2,3-(CH.sub.3).sub.2
69a) non-polar isomer;
oil 3.95(s, 3H); 4.05(s, 3H);
2,4-(CH.sub.3).sub.2 5.05(s, 2H)
69b) polar isomer; oil 3.90(s, 3H); 4.05(s, 3H);
2,4-(CH.sub.3).sub.2 5.05(s, 2H)
70a) non-polar isomer;
oil 3.95(s, 3H); 4.05(s, 3H);
2,5-(CH.sub.3).sub.2 5.05(s, 2H)
70b) polar isomer; 85-88
2,5-(CH.sub.3).sub.2
71a) non-polar isomer;
oil 3.95(s, 3H); 4.05(s, 3H);
2,6-(CH.sub.3).sub.2 4.80(s, 2H)
71b) polar isomer; 79-81
2,6-(CH.sub.3).sub.2
72a) non-polar isomer;
oil 3.95(s, 3H); 4.05(s, 3H);
3,4-(CH.sub.3).sub.2 5.05(s, 2H)
72b) polar isomer; oil 3.90(s, 3H); 4.05(s, 3H);
3,4-(CH.sub.3).sub.2 5.05(s, 2H)
73a) non-polar isomer;
oil 3.95(s, 3H); 4.05(s, 3H);
3,5-(CH.sub.3).sub.2 5.05(s, 2H)
73b) polar isomer; oil 3.90(s, 3H); 4.05(s, 3H);
3,5-(CH.sub.3).sub.2 5.05(s, 2H)
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6,-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-S-C.sub.4 H.sub.9
101 3-S-C.sub.4 H.sub.9
102 4-S-C.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethyl-
butyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2,
6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2, C.sub.6 H.sub.5
137 3-CH.sub.2, C.sub.6 H.sub.5
138 4-CH.sub.2, C.sub.6 H.sub.5
139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub. 3, 4-CH.sub.2 C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158a) 2-OCH.sub.3 ; oil 3.85; 3.90; 5.0(3s, 3H
non-polar isomer in each case); 5.1(s, 2H)
158b) 2-OCH.sub.3 63-67
polar isomer
159a) 3-OCH.sub.3 ; oil 3.80; 3,95; 4.05(3s, 3H
non-polar isomer in each case); 5.1(s, 2H)
159b) 3-OCH.sub.3 35
polar isomer
160a) 4-OCH.sub.3 ; oil 3.75; 3.95; 4.05(3s, 3H
non-polar isomer in each case); 5.05(s, 2H)
160b) 4-OCH.sub.3 75-78
polar isomer
161 3-OC.sub.2 H.sub.5
162 3-O-C.sub.2 H.sub.5
163 4-O-C.sub.2 H.sub.7
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-O-CH.sub.2 C.sub.6 H.sub.5
177 3-O-CH.sub.2 C.sub.6 H.sub.5
178 4-O-CH.sub.2 C.sub.6 H.sub.5
179 2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub. 3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 3-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.2, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
›CHCH H · 4 of 24
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3 ;
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270a) 2-CHNO(n-C.sub.4 H.sub.9);
oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.1(s, 2H)
270b) 2-CHNO(n-C.sub.4 H.sub.9):
oil 3.90(s, 3H); 4.05(s, 3H);
polar isomer 5.1(s, 2H)
271a) 3-CHNO(n-C.sub.4 H.sub.9):
oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.1(s, 2H)
271b) 3-CHNO(n-C.sub.4 H.sub.9):
oil 3.90(s, 3H); 4.05(s, 3H);
polar isomer 5.1(s, 2H)
272a) 4-CHNO(n-C.sub.4 H.sub.9):
oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.05(s, 2H)
272b) 4-CHNO(n-C.sub.4 H.sub.9):
88-89
polar isomer
273a) 2-CHNO(n-C.sub.6 H.sub.13):
oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.1(s, 2H)
273b) 2-CHNO(n-C.sub.6 H.sub.13):
oil 3.90(s, 3H); 4.05(s, 3H);
polar isomer 5.1(s, 2H)
274a) 3-CHNO(n-C.sub.6 H.sub.13):
oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.1(s, 2H)
274b) 3-CHNO(n-C.sub.6 H.sub.13):
oil 3.90(s, 3H); 4.05(s, 3H);
polar isomer 5.1(s, 2H)
275a) 4-CHNO(n-C.sub.6 H.sub.13):
oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.1(s, 2H)
275b) 4-CHNO(n-C.sub.6 H.sub.13):
77-80
polar isomer
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub. 2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (n-C.sub.6 H.sub.13)
295 3-CO.sub.2 (n-C.sub.6 H.sub.13)
296 4-CO.sub.2 (n-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300a) 2-CHNO-allyl: oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.1(s, 2H)
300b) 2-CHNO-allyl: oil 3.90(s, 3H); 4.10(s, 3H);
polar isomer 5.1(s, 2H)
301a) 3-CHNO-allyl: oil 3.95(s, 3H); 4.05(s, 3H);
non-polar isomer 5.1(s, 2H)
301b) 3-CHNO-allyl: oil 3.90(s, 3H); 4.05(s, 3H);
polar isomer 5.1(s, 2H)
302a) 4-CHNO-allyl: oil 3.90(s, 3H); 4.0(s, 3H);
non-polar isomer 5.1(s, 2H)
302b) 4-CHNO-allyl: 89
polar isomer
303 2-CHNO(CH.sub.2).sub.3
(C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3
(C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3
(C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub. 6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR33##
No. X.sub.m mp NMR: δ(ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9 3-Cl
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3 oil 1.75(d, J=8Hz, 3H);
3.7(S, 3H); 5.1(S, 2H)
66 3-CH.sub.3
67 4-CH.sub.3
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub. 3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-SC.sub.4 H.sub.9
101 3-SC.sub.4 H.sub.9
102 4-SC.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub. 4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
›CHCH H · 5 of 24
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2 C.sub.6 H.sub.5
137 3-CH.sub.2 C.sub.6 H.sub.5
138 4-CH.sub.2 C.sub.6 H.sub.5
139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5
141 2-C.sub.6 H.sub. 5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub. 8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
177 3-OCH.sub.2 C.sub.6 H.sub.5
178 4-OCH.sub.2 C.sub.6 H.sub.5
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(n-C.sub.6 H.sub.13)
274 3-CHNO(n-C.sub.6 H.sub.13)
275 4-CHNO(n-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (n-C.sub.6 H.sub.13)
295 3-CO.sub.2 (n-C.sub.6 H.sub.13)
296 4-CO.sub.2 (n-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2 CHCH.sub.2
301 3-CHNOCH.sub.2 CHCH.sub.2
302 4-CHNOCH.sub.2 CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub. 2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR34##
No. X.sub.m mp NMR: δ(ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.4
7 2,3-F.sub.2
8 2-Cl 72-74
9 3-Cl oil 5.0(S, 2H);
7.55(S, 1H)
10 4-Cl 80-81
›CHCH H · 6 of 24
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2 59-61
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2 oil 5.0(S, 2H);
7.55(S, 1H)
16 3,5-Cl.sub.2 93-95
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3 oil 5.0(S, 2H);
7.55(S, 1H)
66 3-CH.sub.3 oil 5.0(S, 2H);
7.55(S, 1H)
67 4-CH.sub.3 69-71
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub. 3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-S-C.sub.4 H.sub.9
101 3-S-C.sub.4 H.sub.9
102 4-S-C.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2 C.sub.6 H.sub.5
137 3-CH.sub.2 C.sub.6 H.sub.5
138 4-CH.sub.2 C.sub.2 H.sub.5
139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-i-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
177 3-OCH.sub.2 C.sub.6 H.sub.5
178 4-OCH.sub.2 C.sub.6 H.sub.5
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 3-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-J.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
›CHCH H · 7 of 24
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(n-C.sub.6 H.sub.13)
274 3-CHNO(n-C.sub.6 H.sub.13)
275 4-CHNO(n-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (n-C.sub.6 H.sub.13)
295 3-CO.sub.2 (n-C.sub.6 H.sub.13)
296 4-CO.sub.2 (n-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2 CHCH.sub.2
301 3-CHNOCH.sub.2 CHCH.sub.2
302 4-CHNOCH.sub.2 CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub. 6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.17)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
333 3-benzoyl oil 5.15(s, 2H);
7.55 (s, 1H)
______________________________________
__________________________________________________________________________
##STR35##
No.
X.sub.m mp NMR: δ (ppm)
__________________________________________________________________________
1a)
2-F: non-polar isomer
oil 3.9(S, 3H); 4.0(S, 3H);
5.15(S, 2H)
1b)
2-F: polar isomer
77-79
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8a)
2-Cl: non-polar isomer
oil 3.9(S, 3H); 4.0(S, 3H);
5.15(S, 2H)
8b)
2-Cl: polar isomer
78-80
9a)
3-Cl: non-polar isomer
oil 3.9(S, 3H); 4.0(S, 3H);
5.05(S, 2H)
9b)
3-Cl: polar isomer
64-66
10a)
4-Cl: non-polar isomer
58-70 3.9(S, 3H); 4.0(S, 3H);
5.0(S, 2H)
10b)
4-Cl: polar isomer
112-120
3.85(S, 3H); 4.05(S, 3H);
5.0(S, 2H)
11
2,3-Cl.sub.2
12a)
2,4-Cl.sub.2 : non-polar isomer
89-93
12b)
2,4-Cl.sub.2 : polar isomer
83-86
13
2,5-Cl.sub.2
14
2,6-Cl.sub.2
15
3,4-Cl.sub.2
16
3,5-Cl.sub.2
17
2,3,4-Cl.sub.3
18
2,3,5-Cl.sub.3
19
2,3,6-Cl.sub.3
20
2,4,5-Cl.sub.3
21
2,4,6-Cl.sub.3
22
3,4,5-Cl.sub.3
23
2,3,4,6-Cl.sub.4
24
2,3,5,6-Cl.sub.4
25
2,3,4,5,6-Cl.sub.5
26
2-Br
27
3-Br
28
4-Br
29
2,4-Br.sub.2
30
2,5-Br.sub.5
31
2,6-Br.sub.2
32
2,4,6-Br.sub.3
33
2,3,4,5,6-Br.sub.5
34
2-I
35
3-I
36
4-I
37
2,4-I.sub.2
38
2-Cl, 3-F
39
2-Cl, 4-F
40
2-Cl, 5-F
41
2-Cl, 6-F
42
2-Cl, 3-Br
43
2-Cl, 4-Br
44
2-Cl, 6-Br
45
2-Cl, 6-Br
46
2-Br, 3-Cl
47
2-Br, 4-Cl
48
2-Br, 5-Cl
49
2-Br, 3-F
50
2-Br, 4-F
51
2-Br, 5-F
52
2-Br, 6-F
53
2-F, 3-Cl
54
2-F, 4-Cl
55
2-F, 5-Cl
56
3-Cl, 4-F
57
3-Cl, 5-F
58
3-Cl, 4-Br
59
3-Cl, 5-Br
60
3-F, 4-Cl
61
3-F, 4-Br
62
3-Br, 4-Cl
63
3-Br, 4-F
64
2,6-Cl.sub.2, 4-Br
65a)
2-CH.sub.3 : non-polar isomer
51-53
65b)
2-CH.sub.3 : polar isomer
79-83
66a
3-CH.sub.3 : non-polar isomer
oil 3.9(s, 3H); 4.0(s, 3H);
5.0(s, 2H)
66b
3-CH.sub.3 : polar isomer
87-89
67a
4-CH.sub.3 : non-polar isomer
oil 3.95(s, 3H); 4.05(s, 3H);
5.05(s, 2H)
67b
3-CH.sub.3 : polar isomer
78-79
68
2,3-(CH.sub.3).sub.2
69
2,4-(CH.sub.3).sub.2
70
2,5-(CH.sub.3).sub.2
71
2,6-(CH.sub.3).sub.2
72
3,4-(CH.sub.3).sub.2
73
3,5-(CH.sub.3).sub.2
74
3,5-(CH.sub.3).sub.2
75
2,3,4-(CH.sub.3).sub.3
76
2,3,6-(CH.sub.3).sub.3
77
2,4,5-(CH.sub.3).sub.3
78
2,4,6-(CH.sub.3).sub.3
79
3,4,5-(CH.sub.3).sub.3
80
2,3,4,6-(CH.sub.3).sub.4
81
2,3,5,6-(CH.sub.3).sub.4
82
2,3,4,5,6-(CH.sub.3).sub.5
83
2-C.sub.2 H.sub.5
84
3-C.sub.2 H.sub.5
85
4-C.sub.2 H.sub.5
86
2,4-(C.sub.2 H.sub.5).sub.2
87
2,6-(C.sub.2 H.sub.5).sub.2
88
3,5-(C.sub.2 H.sub.5).sub. 2
89
2,4,6-(C.sub.2 H.sub.5).sub.3
90
2-n-C.sub.3 H.sub.7
91
3-n-C.sub.3 H.sub.7
92
4-n-C.sub.3 H.sub.7
93
2-i-C.sub.3 H.sub.7
94
3-i-C.sub.3 H.sub.7
95
4-i-C.sub.3 H.sub.7
96
2,4-(i-C.sub.3 H.sub.7).sub.2
97
2,6-(i-C.sub.3 H.sub.7).sub.2
98
3,5-(i-C.sub.3 H.sub.7).sub.2
99
2,4,6-(i-C.sub.3 H.sub.7).sub.3
100
2-S-C.sub.4 H.sub.9
101
3-S-C.sub.4 H.sub.9
102
4-S-C.sub.4 H.sub.9
103
2-t-C.sub.4 H.sub.9
104
3-t-C.sub.4 H.sub.9
105
4-t-C.sub.4 H.sub.9
106
2,3-(t-C.sub.4 H.sub.9).sub.2
107
2,4-(t-C.sub.4 H.sub.9).sub.2
108
2,5-(t-C.sub.4 H.sub.9).sub.2
109
2,6-(t-C.sub.4 H.sub.9).sub.2
110
3,4-(t-C.sub.4 H.sub.9).sub.2
111
2,4,6-(t-C.sub.4 H.sub.9).sub.3
112
4-n-C.sub.9 H.sub.19
113
4-n-C.sub.12 H.sub.25
114
3-n-C.sub.15 H.sub.31
115
4-(1,1,3,3-tetramethylbutyl)
116
4-(2,4,4-trimethylpropyl
117
2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118
2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119
2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120
2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121
2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122
2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123
2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124
3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125
2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126
2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127
2-allyl
128
3-allyl
129
4-allyl
130
2-allyl, 6-CH.sub.3
131
2-cyclo-C.sub.6 H.sub.11
132
3-cyclo-C.sub.6 H.sub.11
133
4-cyclo-C.sub.6 H.sub.11
134
2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135
2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136
2-CH.sub.2 C.sub.6 H.sub.5
137
3-CH.sub.2 C.sub.6 H.sub.5
138
4-CH.sub.2 C.sub.2 H.sub.5
139
2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3
140
2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5
141
2-C.sub.6 H.sub.5
142
3-C.sub.6 H.sub.5
143
4-C.sub.6 H.sub.5
144
4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)
145
4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
›CHCH H · 8 of 24
146
2-Cl, 4-C.sub.6 H.sub.5
147
2-Br, 4-C.sub.6 H.sub.5
148
2-C.sub.6 H.sub.5, 4-Cl
149
2-C.sub.6 H.sub.5 , 4-Br
150
2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151
2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152
2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153
2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154
2-cyclo-C.sub.6 H.sub.11, 4-Cl
155
2-cyclo-C.sub.6 H.sub.11, 4-Br
156
2-Cl, 4-cyclo-C.sub.6 H.sub.11
157
2-Br, 4-cyclo-C.sub.6 H.sub.11
158
2-OCH.sub.3
159a
3-OCH.sub.3 : oil 3.80; 3, 95, 4.05(3s, 3H
non-polar isomer in each case); 5.05(s, 2H)
159b
3-OCH.sub.3 : oil 3.80; 3.90, 4.05(3s, 3H
polar isomer in each case); 5.05(s, 2H)
160
4-OCH.sub.3
161
2-OC.sub.2 H.sub.5
162
3-O-C.sub.2 H.sub.5
163
4-O-C.sub.2 H.sub.5
164
2-O-n-C.sub.3 H.sub.7
165
3-O-n-C.sub.3 H.sub.7
166
4-O-n-C.sub.3 H.sub.7
167
2-O-i-C.sub.3 H.sub.7
168
3-O-i-C.sub.3 H.sub.7
169
4-O-i-C.sub.3 H.sub.7
170
2-O-n-C.sub.6 H.sub.13
171
3-O-n-C.sub.6 H.sub.13
172
4-O-n-C.sub.6 H.sub.13
173
2-O-n-C.sub.8 H.sub.17
174
3-O-n-C.sub.8 H.sub.17
175
4-O-n-C.sub.8 H.sub.17
176
2-O-CH.sub.2 C.sub.6 H.sub.5
177
3-O-CH.sub.2 C.sub.6 H.sub.5
178
4-O-CH.sub.2 C.sub.6 H.sub. 5
179
2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
180
3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
181
4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
182
2,4-(OCH.sub.3).sub.2
183
2-CF.sub.3
184
3-CF.sub.3
185
4-CF.sub.3
186
2-OCF.sub.3
187
3-OCF.sub.3
188
4-OCF.sub.3
189
3-OCH.sub.2 CHF.sub.2
190
2-NO.sub.2
191
3-NO.sub.2
192
4-NO.sub.2
193
2-CN
194
3-CN
195
4-CN
196
2-CH.sub.3, 3-Cl
197
2-CH.sub.3, 4-Cl
198
2-CH.sub.3, 5-Cl
199
2-CH.sub.3, 6-Cl
200
2-CH.sub.3, 3-F
201
2-CH.sub.3, 4-F
202
2-CH.sub.3, 5-F
203
2-CH.sub.3, 6-F
204
2-CH.sub.3, 3-Br
205
2-CH.sub.3, 4-Br
206
2-CH.sub.3, 5-Br
207
2-CH.sub.3, 6-Br
208
2-Cl, 3-CH.sub.3
209
2-Cl, 4-CH.sub.3
210
2-Cl, 5-CH.sub.3
211
2-F, 3-CH.sub.3
212
2-F, 4-CH.sub.3
213
2-F, 5-CH.sub.3
214
2-Br, 3-CH.sub.3
215
2-Br, 4-CH.sub.3
216
2-Br, 5-CH.sub.3
217
3-CH.sub.3, 4-Cl
218
3-CH.sub.3, 5-Cl
219
3-CH.sub.3, 4-F
220
3-CH.sub.3, 4-Br
221
3-CH.sub.3, 4-Br
222
3-CH.sub.3, 5-Br
223
3-F, 4-CH.sub. 3
224
3-Cl, 4-CH.sub.3
225
3-Br, 4-CH.sub.3
226
2-Cl, 4,5-(CH.sub.3).sub.2
227
2-Br, 4,5-(CH.sub.3).sub.2
228
2-Cl, 3,5-(CH.sub.3).sub.2
229
2-Br, 3,5-(CH.sub.3).sub.2
230
2,6-Cl.sub.2, 4-CH.sub.3
231
2,6-F.sub.2, 4-CH.sub.3
232
2,6-Br.sub.2, 4-CH.sub.3
233
2,4-Cl.sub.2, 6-CH.sub.3
234
2,4-F.sub.2, 6-CH.sub.3
235
2,4-Br.sub.2, 6-CH.sub.3
236
2,6-(CH.sub.3).sub.2, 4-F
237
2,6-(CH.sub.3).sub.2, 4-Cl
238
2,6-(CH.sub.3).sub.2, 4-Br
239
3,5-(CH.sub.3).sub.2, 4-F
240
3,5-(CH.sub.3).sub.2, 4-Cl
241
3,5-(CH.sub.3).sub.2, 4-Br
242
2,3,6-(CH.sub.3).sub.3, 4-F
243
2,3,6-(CH.sub.3).sub.3, 4-Cl
244
2,3,6-(CH.sub.3).sub.3, 4-Br
245
2,4-(CH.sub.3).sub.2, 6-F
246
2,4-(CH.sub.3).sub.2, 6-Cl
247
2,4-(CH.sub.3).sub.62, 6-Br
248
2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249
2-Cl, 4-NO.sub.2
250
2-NO.sub.2, 4-Cl
251
2-OCH.sub.3, 5-NO.sub.2
252
2,4-Cl.sub.2, 5-NO.sub.2
253
2,4-Cl.sub.2, 6-NO.sub.2
254
2,6-Cl.sub.2, 4-NO.sub.2
255
2,6-Br.sub.2, 4-NO.sub. 2
256
2,6-I.sub.2, 4-NO.sub.2
257
2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258
2-C.sub.6 H.sub.5 O
259
3-C.sub.6 H.sub.5 O
260
4-C.sub.6 H.sub.5 O
261
2-CHNOCH.sub.3
262
3-CHNOCH.sub.3
263
4-CHNOCH.sub.3
264
2-CHNOC.sub.2 H.sub.5
265
3-CHNOC.sub.2 H.sub.5
266
4-CHNOC.sub.2 H.sub.5
267
2-CHNO(n-C.sub.3 H.sub.7)
268
3-CHNO(n-C.sub.3 H.sub.7)
269
4-CHNO(n-C.sub.3 H.sub.7)
270
2-CHNO(i-C.sub.3 H.sub.7)
271
3-CHNO(i-C.sub.3 H.sub.7)
272
4-CHNO(i-C.sub.3 H.sub.7)
273
2-CHNO(n-C.sub.6 H.sub.13)
274
3-CHNO(n-C.sub.6 H.sub.13)
275
4-CHNO(n-C.sub.6 H.sub.13)
276
2-CHNO(n-C.sub.8 H.sub.17)
277
3-CHNO(n-C.sub.8 H.sub.17)
278
4-CHNO(n-C.sub.8 H.sub.17)
279
2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280
3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281
4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282
2-CO.sub.2 CH.sub.3
283
3-CO.sub.2 CH.sub.3
284
4-CO.sub.2 CH.sub.3
285
2-CO.sub.2 (C.sub.2 H.sub.5)
286
3-CO.sub.2 (C.sub.2 H.sub.5)
287
4-CO.sub.2 (C.sub.2 H.sub.5)
288
2-CO.sub.2 (n-C.sub.3 H.sub. 7)
289
3-CO.sub.2 (n-C.sub.3 H.sub.7)
290
4-CO.sub.2 (n-C.sub.3 H.sub.7)
291
2-CO.sub.2 (i-C.sub.3 H.sub.7)
292
3-CO.sub.2 (i-C.sub.3 H.sub.7)
293
4-CO.sub.2 (i-C.sub.3 H.sub.7)
294
2-CO.sub.2 (n-C.sub.6 H.sub.13)
295
3-CO.sub.2 (n-C.sub.6 H.sub.13)
296
4-CO.sub.2 (n-C.sub.6 H.sub.13)
297
2-CO.sub.2 (n-C.sub.8 H.sub.17)
298
3-CO.sub.2 (n-C.sub.8 H.sub.17)
299
4-CO.sub.2 (n-C.sub.8 H.sub.17)
300
2-CHNOCH.sub.2 CHCH.sub.2
301
3-CHNOCH.sub.2 CHCH.sub.2
302
4-CHNOCH.sub.2 CHCH.sub.2
303
2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304
3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305
4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306
2-CH.sub.2 OCH.sub.3
307
3-CH.sub.2 OCH.sub.3
308
4-CH.sub.2 OCH.sub.3
309
2-CH.sub.2 O(C.sub.2 H.sub.5)
310
3-CH.sub.2 O(C.sub.2 H.sub.5)
311
4-CH.sub.2 O(C.sub.2 H.sub.5)
312
2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313
3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314
4-CH.sub.2 O(n-C.sub.3 H.sub.7 )
315
2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316
3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317
4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318
2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319
3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320
4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321
2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322
3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323
4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324
2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325
3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326
4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327
2-CH.sub.2 O(CH.sub.2).sub.3
328
3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329
4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330
2-CHO
331
3-CHO
332
4-CHO
__________________________________________________________________________
______________________________________
##STR36##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6,-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9 3-Cl
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6,-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
›CHCH H · 9 of 24
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3
66 3-CH.sub.3
67 4-CH.sub.3
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3 ).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-S-C.sub.4 H.sub.9
101 3-S-C.sub.4 H.sub.9
102 4-S-C.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2 -C.sub.6 H.sub.5
137 3-CH.sub.2 -C.sub.6 H.sub.5
138 4-CH.sub.2 -C.sub.2 H.sub.5
139 2-CH.sub.2 -C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2 -C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7 -C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 5-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-O-C.sub.2 H.sub.5
163 4-O-C.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-O-CH.sub.2 C.sub.6 H.sub.5
177 3-O-CH.sub.2 C.sub.6 H.sub.5
178 4-O-CH.sub.2 C.sub.6 H.sub.5
179 2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3)62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2 , 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(n-C.sub.6 H.sub.13)
274 3-CHNO(n-C.sub.6 H.sub.13)
275 4-CHNO(n-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
›CHCH H · 10 of 24
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (n-C.sub.6 H.sub.13)
295 3-CO.sub.2 (n-C.sub.6 H.sub.13)
296 4-CO.sub.2 (n-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2 CHCH.sub.2
301 3-CHNOCH.sub.2 CHCH.sub.2
302 4-CHNOCH.sub.2 CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR37##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9 3-Cl
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3
66 3-CH.sub.3
67 4-CH.sub.3
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub. 2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-SC.sub.4 H.sub.9
101 3-SC.sub.4 H.sub.9
102 4-SC.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2C.sub.6 H.sub.5
137 3-CH.sub.2C.sub.6 H.sub.5
138 4-CH.sub.2C.sub.6 H.sub.5
139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
177 3-OCH.sub.2 C.sub.6 H.sub.5
178 4-OCH.sub.2 C.sub.6 H.sub.5
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
›CHCH H · 11 of 24
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub. 3 H.sub.7)
273 2-CHNO(i-C.sub.6 H.sub.13)
274 3-CHNO(i-C.sub.6 H.sub.13)
275 4-CHNO(i-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (i-C.sub.6 H.sub.13)
295 3-CO.sub.2 (i-C.sub.6 H.sub.13)
296 4-CO.sub.2 (i-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2CHCH.sub.2
301 3-CHNOCH.sub.2CHCH.sub.2
302 4-CHNOCH.sub.2CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR38##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9 3-Cl
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3
66 3-CH.sub.3
67 4-CH.sub.3
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-SC.sub.4 H.sub.9
101 3-SC.sub.4 H.sub.9
102 4-SC.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
›CHCH H · 12 of 24
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub. 3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2C.sub.6 H.sub.5
137 3-CH.sub.2C.sub.6 H.sub.5
138 4-CH.sub.2C.sub.6 H.sub.5
139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
177 3-OCH.sub.2 C.sub.6 H.sub.5
178 4-OCH.sub.2 C.sub.6 H.sub.5
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub. 3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(i-C.sub.6 H.sub.13)
274 3-CHNO(i-C.sub.6 H.sub.13)
275 4-CHNO(i-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (i-C.sub.6 H.sub.13)
295 3-CO.sub.2 (i-C.sub.6 H.sub.13)
296 4-CO.sub.2 (i-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNO CH.sub.2CHCH.sub.2
301 3-CHNOCH.sub.2CHCH.sub.2
302 4-CHNOCH.sub.2CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub. 6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
›CHCH H · 13 of 24
______________________________________
##STR39##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9 3-Cl
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3
66 3-CH.sub.3
67 4-CH.sub.3
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-SC.sub.4 H.sub.9
101 3-SC.sub.4 H.sub.9
102 4-SC.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub. 3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2C.sub.6 H.sub.5
137 3-CH.sub.2C.sub.6 H.sub.5
138 4-CH.sub.2C.sub.6 H.sub.5
139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
177 3-OCH.sub.2 C.sub.6 H.sub.5
178 4-OCH.sub.2 C.sub.6 H.sub.5
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub. 3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
›CHCH H · 14 of 24
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(i-C.sub.6 H.sub.13)
274 3-CHNO(i-C.sub.6 H.sub.13)
275 4-CHNO(i-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (i-C.sub.6 H.sub.13)
295 3-CO.sub.2 (i-C.sub.6 H.sub.13)
296 4-CO.sub.2 (i-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNO CH.sub.2CHCH.sub.2
301 3-CHNOCH.sub.2CHCH.sub.2
302 4-CHNOCH.sub.2CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub. 6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR40##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl 83-85
9 3-Cl oil 5.35(S, 2H);
7.6(S, 1H)
10 4-Cl oil 5.35(S, 2H);
7.6(S, 1H)
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3 68-69
66 3-CH.sub.3 oil 5.35(S, 2H);
7.55(S, 1H)
67 4-CH.sub.3 oil 5.35(S, 2H);
7.55(S, 1H)
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-SC.sub.4 H.sub.9
101 3-SC.sub.4 H.sub.9
102 4-SC.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub. 3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2C.sub.6 H.sub.5
137 3-CH.sub.2C.sub.6 H.sub.5
138 4-CH.sub.2C.sub.6 H.sub.5
139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3 89-91
159 3-OCH.sub.3 72-73
›CHCH H · 15 of 24
160 4-OCH.sub.3 oil 5.35(S, 2H);
7.55(S, 1H)
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
oil 5.35(S, 2H);
7.55(S, 1H)
165 3-O-n-C.sub.3 H.sub.7
oil 5.35(S, 2H);
7.55(S, 1H)
166 4-O-n-C.sub.3 H.sub.7
73-74
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
oil 5.35(S, 2H);
7.55(S, 1H)
171 3-O-n-C.sub.6 H.sub.13
43-45
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
oil 5.35(S, 2H);
7.55(S, 1H)
177 3-OCH.sub.2 C.sub.6 H.sub.5
oil 5.35(S, 2H);
7.55(S, 1H)
178 4-OCH.sub.2 C.sub.6 H.sub.5
103-106
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
oil 5.35(S, 2H);
7.55(S, 1H)
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
oil 5.35(S, 2H);
7.55(S, 1H)
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
oil 5.35(S, 2H);
7.55(S, 1H)
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 4-CH.sub.3
234 2,4-F.sub.2, 4-CH.sub.3
235 2,4-Br.sub.2, 4-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(i-C.sub.6 H.sub.13)
274 3-CHNO(i-C.sub.6 H.sub.13)
275 4-CHNO(i-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (i-C.sub.6 H.sub.13)
295 3-CO.sub.2 (i-C.sub.6 H.sub.13)
296 4-CO.sub.2 (i-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2CHCH.sub.2
301 3-CHNOCH.sub.2CHCH.sub.2
302 4-CHNOCH.sub.2CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub. 2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR41##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9 3-Cl
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3
66a) 3-CH.sub.3 : non-polar isomer
oil 3.9(S, 3H); 4.0(S, 3H);
5.15(S, 2H)
66b) 3-CH.sub.3 : polar isomer
›CHCH H · 16 of 24
66-70
67 4-CH.sub.3
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-SC.sub.4 H.sub.9
101 3-SC.sub.4 H.sub.9
102 4-SC.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub. 3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2C.sub.6 H.sub.5
137 3-CH.sub.2C.sub.6 H.sub.5
138 4-CH.sub.2C.sub.2 H.sub.5
139 2-CH.sub.2C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-OC.sub.2 H.sub.5
163 4-OC.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-OCH.sub.2 C.sub.6 H.sub.5
177 3-OCH.sub.2 C.sub.6 H.sub.5
178 4-OCH.sub.2 C.sub.6 H.sub.5
179 2-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub. 2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub.3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub. 5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(n-C.sub.6 H.sub.13)
274 3-CHNO(n-C.sub.6 H.sub.13)
275 4-CHNO(n-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (n-C.sub.6 H.sub.13)
›CHCH H · 17 of 24
295 3-CO.sub.2 (n-C.sub.6 H.sub.13)
296 4-CO.sub.2 (n-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2CHCH.sub.2
301 3-CHNOCH.sub.2CHCH.sub.2
302 4-CHNOCH.sub.2CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub.7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub. 17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR42##
No. X.sub.m mp NMR: δ (ppm)
______________________________________
1 2-F
2 3-F
3 4-F
4 2,4-F.sub.2
5 2,4,6-F.sub.3
6 2,3,4,5,6-F.sub.5
7 2,3-F.sub.2
8 2-Cl
9 3-Cl
10 4-Cl
11 2,3-Cl.sub.2
12 2,4-Cl.sub.2
13 2,5-Cl.sub.2
14 2,6-Cl.sub.2
15 3,4-Cl.sub.2
16 3,5-Cl.sub.2
17 2,3,4-Cl.sub.3
18 2,3,5-Cl.sub.3
19 2,3,6-Cl.sub.3
20 2,4,5-Cl.sub.3
21 2,4,6-Cl.sub.3
22 3,4,5-Cl.sub.3
23 2,3,4,6-Cl.sub.4
24 2,3,5,6-Cl.sub.4
25 2,3,4,5,6-Cl.sub.5
26 2-Br
27 3-Br
28 4-Br
29 2,4-Br.sub.2
30 2,5-Br.sub.5
31 2,6-Br.sub.2
32 2,4,6-Br.sub.3
33 2,3,4,5,6-Br.sub.5
34 2-I
35 3-I
36 4-I
37 2,4-I.sub.2
38 2-Cl, 3-F
39 2-Cl, 4-F
40 2-Cl, 5-F
41 2-Cl, 6-F
42 2-Cl, 3-Br
43 2-Cl, 4-Br
44 2-Cl, 6-Br
45 2-Cl, 6-Br
46 2-Br, 3-Cl
47 2-Br, 4-Cl
48 2-Br, 5-Cl
49 2-Br, 3-F
50 2-Br, 4-F
51 2-Br, 5-F
52 2-Br, 6-F
53 2-F, 3-Cl
54 2-F, 4-Cl
55 2-F, 5-Cl
56 3-Cl, 4-F
57 3-Cl, 5-F
58 3-Cl, 4-Br
59 3-Cl, 5-Br
60 3-F, 4-Cl
61 3-F, 4-Br
62 3-Br, 4-Cl
63 3-Br, 4-F
64 2,6-Cl.sub.2, 4-Br
65 2-CH.sub.3
66 3-CH.sub.3
67 4-CH.sub.3
68 2,3-(CH.sub.3).sub.2
69 2,4-(CH.sub.3).sub.2
70 2,5-(CH.sub.3).sub.2
71 2,6-(CH.sub.3).sub.2
72 3,4-(CH.sub.3).sub.2
73 3,5-(CH.sub.3).sub.2
74 3,5-(CH.sub.3).sub.2
75 2,3,4-(CH.sub.3).sub.3
76 2,3,6-(CH.sub.3).sub.3
77 2,4,5-(CH.sub.3).sub.3
78 2,4,6-(CH.sub.3).sub.3
79 3,4,5-(CH.sub.3).sub.3
80 2,3,4,6-(CH.sub.3).sub.4
81 2,3,5,6-(CH.sub.3).sub.4
82 2,3,4,5,6-(CH.sub.3).sub.5
83 2-C.sub.2 H.sub.5
84 3-C.sub.2 H.sub.5
85 4-C.sub.2 H.sub.5
86 2,4-(C.sub.2 H.sub.5).sub.2
87 2,6-(C.sub.2 H.sub.5).sub.2
88 3,5-(C.sub.2 H.sub.5).sub.2
89 2,4,6-(C.sub.2 H.sub.5).sub.3
90 2-n-C.sub.3 H.sub.7
91 3-n-C.sub.3 H.sub.7
92 4-n-C.sub.3 H.sub.7
93 2-i-C.sub.3 H.sub.7
94 3-i-C.sub.3 H.sub.7
95 4-i-C.sub.3 H.sub.7
96 2,4-(i-C.sub.3 H.sub.7).sub.2
97 2,6-(i-C.sub.3 H.sub.7).sub.2
98 3,5-(i-C.sub.3 H.sub.7).sub.2
99 2,4,6-(i-C.sub.3 H.sub.7).sub.3
100 2-S-C.sub.4 H.sub.9
101 3-S-C.sub.4 H.sub.9
102 4-S-C.sub.4 H.sub.9
103 2-t-C.sub.4 H.sub.9
104 3-t-C.sub.4 H.sub.9
105 4-t-C.sub.4 H.sub.9
106 2,3-(t-C.sub.4 H.sub.9).sub.2
107 2,4-(t-C.sub.4 H.sub.9).sub.2
108 2,5-(t-C.sub.4 H.sub.9).sub.2
109 2,6-(t-C.sub.4 H.sub.9).sub.2
110 3,4-(t-C.sub.4 H.sub.9).sub.2
111 2,4,6-(t-C.sub.4 H.sub.9).sub.3
112 4-n-C.sub.9 H.sub.19
113 4-n-C.sub.12 H.sub.25
114 3-n-C.sub.15 H.sub.31
115 4-(1,1,3,3-tetramethylbutyl)
116 4-(2,4,4-trimethylpropyl
117 2-t-C.sub.4 H.sub.9, 4-CH.sub.3
118 2-t-C.sub.4 H.sub.9, 5-CH.sub.3
119 2,6-(t-C.sub.4 H.sub.9), 4-CH.sub.3
120 2-CH.sub.3, 4-t-C.sub.4 H.sub.9
121 2-CH.sub.3, 6-t-C.sub.4 H.sub.9
122 2-CH.sub.3, 4-i-C.sub.3 H.sub.7
123 2-CH.sub.3, 5-i-C.sub.3 H.sub.7
124 3-CH.sub.3, 4-i-C.sub.3 H.sub.7
125 2-i-C.sub.3 H.sub.7, 5 CH.sub.3
126 2,4-(t-C.sub.4 H.sub.9), 6-i-C.sub.3 H.sub.7
127 2-allyl
128 3-allyl
129 4-allyl
130 2-allyl, 6-CH.sub.3
131 2-cyclo-C.sub.6 H.sub.11
132 3-cyclo-C.sub.6 H.sub.11
133 4-cyclo-C.sub.6 H.sub.11
134 2,4-(cyclo-C.sub.6 H.sub.11).sub.2, 6-CH.sub.3
135 2-CH.sub.3, 4-cyclo-C.sub.6 H.sub.11
136 2-CH.sub.2 C.sub.6 H.sub.5
137 3-CH.sub.2 C.sub.6 H.sub.5
138 4-CH.sub.2 C.sub.2 H.sub.5
139 2-CH.sub.2 C.sub.6 H.sub.5, 4-CH.sub.3
140 2-CH.sub.3, 4-CH.sub.2 C.sub.6 H.sub.5
141 2-C.sub.6 H.sub.5
142 3-C.sub.6 H.sub.5
143 4-C.sub.6 H.sub.5
144 4-(2-i-C.sub.3 H.sub.7 C.sub.6 H.sub.4)
145 4-C.sub.6 H.sub.5, 2,6-(CH.sub.3).sub.2
146 2-Cl, 4-C.sub.6 H.sub.5
147 2-Br, 4-C.sub.6 H.sub.5
148 2-C.sub.6 H.sub.5, 4-Cl
149 2-C.sub.6 H.sub.5, 4-Br
150 2-CH.sub.2 C.sub.6 H.sub.5, 4-Cl
151 2-CH.sub.2 C.sub.6 H.sub.5, 4-Br
152 2-Cl, 4-CH.sub.2 C.sub.6 H.sub.5
153 2-Br, 4-CH.sub.2 C.sub.6 H.sub.5
154 2-cyclo-C.sub.6 H.sub.11, 4-Cl
155 2-cyclo-C.sub.6 H.sub.11, 4-Br
156 2-Cl, 4-cyclo-C.sub.6 H.sub.11
157 2-Br, 4-cyclo-C.sub.6 H.sub.11
158 2-OCH.sub.3
159 3-OCH.sub.3
160 4-OCH.sub.3
161 2-OC.sub.2 H.sub.5
162 3-O-C.sub.2 H.sub.5
163 4-O-C.sub.2 H.sub.5
164 2-O-n-C.sub.3 H.sub.7
165 3-O-n-C.sub.3 H.sub.7
166 4-O-n-C.sub.3 H.sub.7
167 2-O-i-C.sub.3 H.sub.7
168 3-O-i-C.sub.3 H.sub.7
169 4-O-i-C.sub.3 H.sub.7
170 2-O-n-C.sub.6 H.sub.13
171 3-O-n-C.sub.6 H.sub.13
172 4-O-n-C.sub.6 H.sub.13
173 2-O-n-C.sub.8 H.sub.17
174 3-O-n-C.sub.8 H.sub.17
175 4-O-n-C.sub.8 H.sub.17
176 2-O-CH.sub.2 C.sub.6 H.sub.5
177 3-O-CH.sub. 2 C.sub.6 H.sub.5
178 4-O-CH.sub.2 C.sub.6 H.sub.5
179 2-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
180 3-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
181 4-O-(CH.sub.2).sub.3 C.sub.6 H.sub.5
182 2,4-(OCH.sub.3).sub.2
183 2-CF.sub.3
184 3-CF.sub.3
185 4-CF.sub.3
186 2-OCF.sub.3
187 3-OCF.sub.3
188 4-OCF.sub.3
189 3-OCH.sub.2 CHF.sub.2
190 2-NO.sub.2
191 3-NO.sub.2
192 4-NO.sub.2
193 2-CN
194 3-CN
195 4-CN
196 2-CH.sub.3, 3-Cl
197 2-CH.sub.3, 4-Cl
198 2-CH.sub.3, 5-Cl
199 2-CH.sub.3, 6-Cl
200 2-CH.sub.3, 3-F
201 2-CH.sub.3, 4-F
202 2-CH.sub.3, 5-F
203 2-CH.sub.3, 6-F
204 2-CH.sub.3, 3-Br
205 2-CH.sub.3, 4-Br
206 2-CH.sub.3, 5-Br
207 2-CH.sub.3, 6-Br
208 2-Cl, 3-CH.sub.3
209 2-Cl, 4-CH.sub.3
210 2-Cl, 5-CH.sub.3
›CHCH H · 18 of 24
211 2-F, 3-CH.sub.3
212 2-F, 4-CH.sub.3
213 2-F, 5-CH.sub.3
214 2-Br, 3-CH.sub.3
215 2-Br, 4-CH.sub.3
216 2-Br, 5-CH.sub.3
217 3-CH.sub.3, 4-Cl
218 3-CH.sub.3, 5-Cl
219 3-CH.sub.3, 4-F
220 3-CH.sub.3, 4-Br
221 3-CH.sub. 3, 4-Br
222 3-CH.sub.3, 5-Br
223 3-F, 4-CH.sub.3
224 3-Cl, 4-CH.sub.3
225 3-Br, 4-CH.sub.3
226 2-Cl, 4,5-(CH.sub.3).sub.2
227 2-Br, 4,5-(CH.sub.3).sub.2
228 2-Cl, 3,5-(CH.sub.3).sub.2
229 2-Br, 3,5-(CH.sub.3).sub.2
230 2,6-Cl.sub.2, 4-CH.sub.3
231 2,6-F.sub.2, 4-CH.sub.3
232 2,6-Br.sub.2, 4-CH.sub.3
233 2,4-Cl.sub.2, 6-CH.sub.3
234 2,4-F.sub.2, 6-CH.sub.3
235 2,4-Br.sub.2, 6-CH.sub.3
236 2,6-(CH.sub.3).sub.2, 4-F
237 2,6-(CH.sub.3).sub.2, 4-Cl
238 2,6-(CH.sub.3).sub.2, 4-Br
239 3,5-(CH.sub.3).sub.2, 4-F
240 3,5-(CH.sub.3).sub.2, 4-Cl
241 3,5-(CH.sub.3).sub.2, 4-Br
242 2,3,6-(CH.sub.3).sub.3, 4-F
243 2,3,6-(CH.sub.3).sub.3, 4-Cl
244 2,3,6-(CH.sub.3).sub.3, 4-Br
245 2,4-(CH.sub.3).sub.2, 6-F
246 2,4-(CH.sub.3).sub.2, 6-Cl
247 2,4-(CH.sub.3).sub.62, 6-Br
248 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3
249 2-Cl, 4-NO.sub.2
250 2-NO.sub.2, 4-Cl
251 2-OCH.sub.3, 5-NO.sub.2
252 2,4-Cl.sub.2, 5-NO.sub.2
253 2,4-Cl.sub.2, 6-NO.sub.2
254 2,6-Cl.sub.2, 4-NO.sub.2
255 2,6-Br.sub.2, 4-NO.sub.2
256 2,6-I.sub.2, 4-NO.sub.2
257 2-CH.sub.3, 5-i-C.sub.3 H.sub.7, 4-Cl
258 2-C.sub.6 H.sub.5 O
259 3-C.sub.6 H.sub.5 O
260 4-C.sub.6 H.sub.5 O
261 2-CHNOCH.sub.3
262 3-CHNOCH.sub.3
263 4-CHNOCH.sub.3
264 2-CHNOC.sub.2 H.sub.5
265 3-CHNOC.sub.2 H.sub.5
266 4-CHNOC.sub.2 H.sub.5
267 2-CHNO(n-C.sub.3 H.sub.7)
268 3-CHNO(n-C.sub.3 H.sub.7)
269 4-CHNO(n-C.sub.3 H.sub.7)
270 2-CHNO(i-C.sub.3 H.sub.7)
271 3-CHNO(i-C.sub.3 H.sub.7)
272 4-CHNO(i-C.sub.3 H.sub.7)
273 2-CHNO(n-C.sub.6 H.sub.13)
274 3-CHNO(n-C.sub.6 H.sub.13)
275 4-CHNO(n-C.sub.6 H.sub.13)
276 2-CHNO(n-C.sub.8 H.sub.17)
277 3-CHNO(n-C.sub.8 H.sub.17)
278 4-CHNO(n-C.sub.8 H.sub.17)
279 2-CHNOCH.sub.2 (C.sub.6 H.sub.5)
280 3-CHNOCH.sub.2 (C.sub.6 H.sub.5)
281 4-CHNOCH.sub.2 (C.sub.6 H.sub.5)
282 2-CO.sub.2 CH.sub.3
283 3-CO.sub.2 CH.sub.3
284 4-CO.sub.2 CH.sub.3
285 2-CO.sub.2 (C.sub.2 H.sub.5)
286 3-CO.sub.2 (C.sub.2 H.sub.5)
287 4-CO.sub.2 (C.sub.2 H.sub.5)
288 2-CO.sub.2 (n-C.sub.3 H.sub.7)
289 3-CO.sub.2 (n-C.sub.3 H.sub.7)
290 4-CO.sub.2 (n-C.sub.3 H.sub.7)
291 2-CO.sub.2 (i-C.sub.3 H.sub.7)
292 3-CO.sub.2 (i-C.sub.3 H.sub.7)
293 4-CO.sub.2 (i-C.sub.3 H.sub.7)
294 2-CO.sub.2 (n-C.sub.6 H.sub.13)
295 3-CO.sub.2 (n-C.sub.6 H.sub.13)
296 4-CO.sub.2 (n-C.sub.6 H.sub.13)
297 2-CO.sub.2 (n-C.sub.8 H.sub.17)
298 3-CO.sub.2 (n-C.sub.8 H.sub.17)
299 4-CO.sub.2 (n-C.sub.8 H.sub.17)
300 2-CHNOCH.sub.2 CHCH.sub.2
301 3-CHNOCH.sub.2 CHCH.sub.2
302 4-CHNOCH.sub.2 CHCH.sub.2
303 2-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
304 3-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
305 4-CHNO(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
306 2-CH.sub.2 OCH.sub.3
307 3-CH.sub.2 OCH.sub.3
308 4-CH.sub.2 OCH.sub.3
309 2-CH.sub.2 O(C.sub.2 H.sub.5)
310 3-CH.sub.2 O(C.sub.2 H.sub.5)
311 4-CH.sub.2 O(C.sub.2 H.sub.5)
312 2-CH.sub.2 O(n-C.sub.3 H.sub. 7)
313 3-CH.sub.2 O(n-C.sub.3 H.sub.7)
314 4-CH.sub.2 O(n-C.sub.3 H.sub.7)
315 2-CH.sub.2 O(i-C.sub.3 H.sub.7)
316 3-CH.sub.2 O(i-C.sub.3 H.sub.7)
317 4-(CH.sub.2 O(i-C.sub.3 H.sub.7)
318 2-CH.sub.2 O(n-C.sub.6 H.sub.13)
319 3-CH.sub.2 O(n-C.sub.6 H.sub.13)
320 4-CH.sub.2 O(n-C.sub.6 H.sub.13)
321 2-CH.sub.2 O(n-C.sub.8 H.sub.17)
322 3-CH.sub.2 O(n-C.sub.8 H.sub.17)
323 4-CH.sub.2 O(n-C.sub.8 H.sub.7)
324 2-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
325 3-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
326 4-CH.sub.2 OCH.sub.2 (C.sub.6 H.sub.5)
327 2-CH.sub.2 O(CH.sub.2).sub.3
328 3-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
329 4-CH.sub.2 O(CH.sub.2).sub.3 (C.sub.6 H.sub.5)
330 2-CHO
331 3-CHO
332 4-CHO
______________________________________
______________________________________
##STR43##
No. Aryl mp NMR: δ (ppm)
______________________________________
1 1-naphthyl
2 2-naphthyl
3 3-phenanthrenyl
4 2-chlorophenyl
5 2-bromophenyl
6 3-bromophenyl
7 4-bromophenyl
8 2-fluorophenyl
9 3-fluorophenyl
10 4-fluorophenyl
11 2-ethyl-phenyl
12 3-ethyl-phenyl
13 4-ethyl-phenyl
14 2-iso-propyl-phenyl
15 3-iso-propyl-phenyl
16 4-iso-propyl-phenyl
17 2-tert-butyl-phenyl
18 3-tert-butyl-phenyl
19 4-tert-butyl-phenyl
20 4-butyl-phenyl
21 4-hexyl-phenyl
22 4-nonyl-phenyl
23 4-decyl-phenyl
24 2-methoxy-phenyl
25 3-methoxy-phenyl
26 4-methoxy-phenyl
27 2-trifluoromethyl-phenyl
28 3-trifluoromethyl-phenyl
29 4-trifluoromethyl-phenyl
30 4-formyl-phenyl
31 2-nitro-phenyl
32 3-nitro-phenyl
33 4-nitro-phenyl
34 2,5-dichlorophenyl
35 2,6-dichlorophenyl
36 3,4-dichlorophenyl
37 2,3-dichlorophenyl
38 3,5-dichlorophenyl
39 2,3,4-trichlorophenyl
40 2,4,5-trichlorophenyl
41 2,4,6-trichlorophenyl
42 2,3,4,6-tetrachlorophenyl
43 2,3,4,5,6-pentachlorophenyl
44 2,3,4,5-tetrafluorophenyl
45 2,3,5,6-tetrafluorophenyl
46 2,3,4,5,6-pentafluorophenyl
47 2-chloro, 4-fluorophenyl
48 3-chloro, 4-fluorophenyl
49 2-chloro, 6-methyl-phenyl
50 4-chloro, 2-methyl-phenyl
51 2,4-dichloro, 5-methyl-phenyl
52 4-chloro, 2,5-dimethyl-phenyl
53 3-bromo, 3-methyl-phenyl
54 3,5-bistrifluoromethyl-phenyl
55 2,5-dimethyl-phenyl
56 2,4-dimethyl-phenyl
57 2,5-dimethyl-phenyl
58 2,6-dimethyl-phenyl
59 3,4-dimethyl-phenyl
60 3,5-dimethyl-phenyl
61 2,4,5-trimethyl-phenyl
62 2,6-diethyl-phenyl
63 2,4-di-tert.-butyl-phenyl
64 2,5-dimethoxy-phenyl
65 3,4-dimethoxy-phenyl
66 2-methyl, 4-tert.-butyl-phenyl
67 2-methoxycarbonyl-phenyl
68 2-ethoxycarbonyl-phenyl
69 2-propoxycarbonyl-phenyl
70 2-butoxycarbonyl-phenyl
71 2-cyano-phenyl
72 3-cyano-phenyl
73 4-cyano-phenyl
______________________________________
______________________________________
##STR44##
No. Aryl mp NMR: δ (ppm)
______________________________________
1 1-naphthyl
2 2-naphthyl
3 3-phenanthrenyl
4 2-chlorophenyl
5 2-bromophenyl
6 3-bromophenyl
7 4-bromophenyl
8 2-fluorophenyl
9 3-fluorophenyl
10 4-fluorophenyl
11 2-ethyl-phenyl
12 3-ethyl-phenyl
13 4-ethyl-phenyl
14 2-iso-propyl-phenyl
15 3-iso-propyl-phenyl
16 4-iso-propyl-phenyl
17 2-tert-butyl-phenyl
18 3-tert-butyl-phenyl
19 4-tert-butyl-phenyl
20 4-butyl-phenyl
21 4-hexyl-phenyl
22 4-nonyl-phenyl
23 4-decyl-phenyl
24 2-methoxy-phenyl
25 3-methoxy-phenyl
26 4-methoxy-phenyl
27 2-trifluoromethyl-phenyl
28 3-trifluoromethyl-phenyl
29 4-trifluoromethyl-phenyl
›CHCH H · 19 of 24
30 4-formyl-phenyl
31 2-nitro-phenyl
32 3-nitro-phenyl
33 4-nitro-phenyl
34 2,5-dichlorophenyl
35 2,6-dichlorophenyl
36 3,4-dichlorophenyl
37 2,3-dichlorophenyl
38 3,5-dichlorophenyl
39 2,3,4-trichlorophenyl
40 2,4,5-trichlorophenyl
41 2,4,6-trichlorophenyl
42 2,3,4,6-tetrachlorophenyl
43 2,3,4,5,6-pentachlorophenyl
44 2,3,4,5-tetrafluorophenyl
45 2,3,5,6-tetrafluorophenyl
46 2,3,4,5,6-pentafluorophenyl
47 2-chloro, 4-fluorophenyl
48 3-chloro, 4-fluorophenyl
49 2-chloro, 6-methyl-phenyl
50 4-chloro, 2-methyl-phenyl
51 2,4-dichloro, 5-methyl-phenyl
52 4-chloro, 2,5-dimethyl-phenyl
53 3-bromo, 3-methyl-phenyl
54 3,5-bistrifluoromethyl-phenyl
55 2,5-dimethyl-phenyl
56 2,4-dimethyl-phenyl
57 2,5-dimethyl-phenyl
58 2,6-dimethyl-phenyl
59 3,4-dimethyl-phenyl
60 3,5-dimethyl-phenyl
61 2,4,5-trimethyl-phenyl
62 2,6-diethyl-phenyl
63 2,4-di-tert.-butyl-phenyl
64 2,5-dimethoxy-phenyl
65 3,4-dimethoxy-phenyl
66 2-methyl, 4-tert.-butyl-phenyl
67 2-methoxycarbonyl-phenyl
68 2-ethoxycarbonyl-phenyl
69 2-propoxycarbonyl-phenyl
70 2-butoxycarbonyl-phenyl
71 2-cyano-phenyl
72 3-cyano-phenyl
73 4-cyano-phenyl
______________________________________
______________________________________
##STR45##
No. Aryl mp NMR: δ (ppm)
______________________________________
1 1-naphthyl
2 2-naphthyl
3 3-phenanthrenyl
4 2-chlorophenyl
5 2-bromophenyl
6 3-bromophenyl
7 4-bromophenyl
8 2-fluorophenyl
9 3-fluorophenyl
10 4-fluorophenyl
11 2-ethyl-phenyl
12 3-ethyl-phenyl
13 4-ethyl-phenyl
14 2-iso-propyl-phenyl
15 3-iso-propyl-phenyl
16 4-iso-propyl-phenyl
17 2-tert-butyl-phenyl
18 3-tert-butyl-phenyl
19 4-tert-butyl-phenyl
20 4-butyl-phenyl
21 4-hexyl-phenyl
22 4-nonyl-phenyl
23 4-decyl-phenyl
24 2-methoxy-phenyl
25 3-methoxy-phenyl
26 4-methoxy-phenyl
27 2-trifluoromethyl-phenyl
28 3-trifluoromethyl-phenyl
29 4-trifluoromethyl-phenyl
30 4-formyl-phenyl
31 2-nitro-phenyl
32 3-nitro-phenyl
33 4-nitro-phenyl
34 2,5-dichlorophenyl
35 2,6-dichlorophenyl
36 3,4-dichlorophenyl
37 2,3-dichlorophenyl
38 3,5-dichlorophenyl
39 2,3,4-trichlorophenyl
40 2,4,5-trichlorophenyl
41 2,4,6-trichlorophenyl
42 2,3,4,6-tetrachlorophenyl
43 2,3,4,5,6-pentachlorophenyl
44 2,3,4,5-tetrafluorophenyl
45 2,3,5,6-tetrafluorophenyl
46 2,3,4,5,6-pentafluorophenyl
47 2-chloro, 4-fluorophenyl
48 3-chloro, 4-fluorophenyl
49 2-chloro, 6-methyl-phenyl
50 4-chloro, 2-methyl-phenyl
51 2,4-dichloro, 5-methyl-phenyl
52 4-chloro, 2,5-dimethyl-phenyl
53 3-bromo, 3-methyl-phenyl
54 3,5-bistrifluoromethyl-phenyl
55 2,5-dimethyl-phenyl
56 2,4-dimethyl-phenyl
57 2,5-dimethyl-phenyl
58 2,6-dimethyl-phenyl
59 3,4-dimethyl-phenyl
60 3,5-dimethyl-phenyl
61 2,4,5-trimethyl-phenyl
62 2,6-diethyl-phenyl
63 2,4-di-tert.-butyl-phenyl
64 2,5-dimethoxy-phenyl
65 3,4-dimethoxy-phenyl
66 2-methyl, 4-tert.-butyl-phenyl
67 2-methoxycarbonyl-phenyl
68 2-ethoxycarbonyl-phenyl
69 2-propoxycarbonyl-phenyl
70 2-butoxycarbonyl-phenyl
71 2-cyano-phenyl
72 3-cyano-phenyl
73 4-cyano-phenyl
______________________________________
__________________________________________________________________________
##STR46##
No.
A Hetaryl mp NMR: δ (ppm)
__________________________________________________________________________
1 CH.sub.2 S
4-pyridyl 76-77
2 CH.sub.2 O
6-methyl-2-pyridyl 76-77
3 CH.sub.2 S
6-methyl-2-pyridyl
4 CH.sub.2 O
6-ethyl-2-pyridyl
5 CH.sub.2 S
6-ethyl-2-pyridyl
6 CH.sub.2 O
6-n-propyl-2-pyridyl
7 CH.sub.2 S
6-n-propyl-2-pyridyl
8 CH.sub.2 O
6-iso-propyl-2-pyridyl
9 CH.sub.2 S
6-iso-propyl-2-pyridyl
10
CH.sub.2 O
6-n-butyl-2-pyridyl
11
CH.sub.2 S
6-n-butyl-2-pyridyl
12
CH.sub.2 O
6-tert.-butyl-2-pyridyl
13
CH.sub.2 S
6-tert.-butyl-2-pyridyl
14
CH.sub.2 O
6-n-pentyl-2-pyridyl
15
CH.sub.2 S
6-n-pentyl-2-pyridyl
16
CH.sub.2 O
6-n-hexyl-2-pyridyl
17
CH.sub.2 S
6-n-hexyl-2-pyridyl
18
CH.sub.2 O
6-phenyl-2-pyridyl
19
CH.sub.2 S
6-phenyl-2-pyridyl
20
CH.sub.2 O
6-benzyl-2-pyridyl
21
CH.sub.2 S
6-benzyl-2-pyridyl
22
CH.sub.2 S
6-benzyl-2-pyridyl
23
CH.sub.2 S
6-trifluoromethyl-2-pyridyl
24
CH.sub.2 O
6-methoxy-2-pyridyl
25
CH.sub.2 S
6-methoxy-2-pyridyl
26
CH.sub.2 O
6-chloro-2-pyridyl 72-73
27
CH.sub.2 S
6-chloro-2-pyridyl
28
CH.sub.2 O
3,6-dimethyl-2-pyridyl
29
CH.sub.2 S
3,6-dimethyl-2-pyridyl
30
CH.sub.2 O
3,6-diethyl-2-pyridyl
31
CH.sub.2 S
3,6-diethyl-2-pyridyl
32
CH.sub.2 O
4,6-dimethyl-2-pyridyl
33
CH.sub.2 S
4,6-dimethyl-2-pyridyl
34
CH.sub.2 O
5,6-dimethyl-2-pyridyl
35
CH.sub.2 S
5,6-dimethyl-2-pyridyl
36
CH.sub.2 O
4-phenyl-6-methyl-2-pyridyl
37
CH.sub.2 S
4-phenyl-6-methyl-2-pyridyl
38
CH.sub.2 O
4,6-diphenyl-2-pyridyl
39
CH.sub.2 S
4,6-diphenyl-2-pyridyl
40
CH.sub.2 O
3,4-dichloro-6-methyl-2-pyridyl
41
CH.sub.2 S
3,4-dichloro-6-methyl-2-pyridyl
42
CH.sub.2 O
3,4,5-trichloro-6-phenyl-2-pyridyl
43
CH.sub.2 S
3,4,5-trichloro-6-phenyl-2-pyridyl
44
CH.sub.2 O
4-trifluoromethyl-6-methyl-2-pyridyl
45
CH.sub.2 S
4-trifluoromethyl-6-methyl-2-pyridyl
46
CH.sub.2 O
3-acetyl-4,6-dimethyl-2-pyridyl
47
CH.sub.2 S
3-acetyl-4,6-dimethyl-2-pyridyl
48
CH.sub.2 O
3-cyano-6-methyl-2-pyridyl
49
CH.sub.2 S
3-cyano-6-methyl-2-pyridyl
50
CH.sub. 2 O
3-cyano-6-ethyl-2-pyridyl
51
CH.sub.2 S
3-cyano-6-ethyl-2-pyridyl
52
CH.sub.2 O
3-cyano-6-n-propyl-2-pyridyl
53
CH.sub.2 S
3-cyano-6-n-propyl-2-pyridyl
54
CH.sub.2 O
3-cyano-6-iso-propyl-2-pyridyl
55
CH.sub.2 S
3-cyano-6-iso-propyl-2-pyridyl
56
CH.sub.2 O
3-cyano-6-cyclo-propyl-2-pyridyl
57
CH.sub.2 S
3-cyano-6-cyclo-propyl-2-pyridyl
58
CH.sub.2 O
3-cyano-6-n-butyl-2-pyridyl
59
CH.sub.2 S
3-cyano-6-n-butyl-2-pyridyl
60
CH.sub.2 O
3-cyano-6-tert.-butyl-2-pyridyl
61
CH.sub.2 S
3-cyano-6-tert.-butyl-2-pyridyl
62
CH.sub.2 O
3-cyano-6-cyclo-hexyl-2-pyridyl
63
CH.sub.2 S
3-cyano-6-cyclo-hexyl-2-pyridyl
64
CH.sub.2 O
3-cyano-6-phenyl-2-pyridyl
65
CH.sub.2 S
3-cyano-6-phenyl-2-pyridyl
66
CH.sub.2 O
3-methyloxycarbonyl-6-iso-propyl-2-pyridyl
67
CH.sub.2 S
3-methyloxycarbonyl-6-iso-propyl-2-pyridyl
68
CH.sub.2 O
3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl
69
CH.sub.2 S
3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl
70
CH.sub.2 O
3-cyano-4,6-dimethyl-2-pyridyl
71
CH.sub.2 S
3-cyano-4,6-dimethyl-2-pyridyl
72
CH.sub.2 O
3,5,6-trichloro-2-pyridyl
73
CH.sub.2 S
3,5,6-trichloro-2-pyridyl
74
CH.sub.2 O
5-trifluoromethyl-2-pyridyl
75
CH.sub.2 S
5-trifluoromethyl-2-pyridyl
76
CH.sub.2 O
3-chloro-5-trifluoromethyl-2-pyridyl
77
CH.sub.2 S
3-chloro-5-trifluoromethyl-2-pyridyl
78
CH.sub.2 O
2-quinolyl
79
CH.sub.2 S
2-quinolyl
80
CH.sub.2 O
›CHCH H · 20 of 24
3-methyl-2-quinolyl
81
CH.sub.2 S
3-methyl-2-quinolyl
82
CH.sub.2 O
4-methyl-2-quinolyl
83
CH.sub.2 S
4-methyl-2-quinolyl
84
CH.sub.2 O
4-ethyl-2-quinolyl
85
CH.sub.2 S
4-ethyl-2-quinolyl
86
CH.sub.2 O
4-phenyl-2-quinolyl
87
CH.sub.2 S
4-phenyl-2-quinolyl
88
CH.sub.2 O
6-methyl-2-quinolyl
89
CH.sub.2 S
6-methyl-2-quinolyl
90
CH.sub.2 O
6-chloro-2-quinolyl
91
Ch.sub.2 S
6-chloro-2-quinolyl
92
CH.sub.2 O
8-methyl-2-quinolyl
93
CH.sub.2 S
8-methyl-2-quinolyl
94
CH.sub.2 O
8-chloro-2-quinolyl
95
CH.sub.2 S
8-chloro-2-quinolyl
96
CH.sub.2 O
4-Ethoxycarbonyl-2-quinolyl
97
CH.sub.2 S
4-Ethoxycarbonyl-2-quinolyl
98
CH.sub.2 O
3,4-dimethyl-2-quinolyl
99
CH.sub.2 S
3,4-dimethyl-2-quinolyl
100
CH.sub.2 O
4-methyl-8-methoxy-2-quinolyl
101
CH.sub.2 S
4-methyl-8-methoxy-2-quinolyl
102
CH.sub.2 O
4-phenyl-8-ethoxy-2-quinolyl
103
CH.sub.2 S
4-phenyl-8-ethoxy-2-quinolyl
104
CH.sub.2 O
4-methyl-8-chloro-2-quinolyl
105
CH.sub.2 S
4-methyl-8-chloro-2-quinolyl
106
CH.sub.2 O
4-methyl-8-fluoro-2-quinolyl
107
CH.sub.2 S
4-methyl-8-fluoro-2-quinolyl
108
CH.sub.2 O
4-quinolyl
109
CH.sub.2 S
4-quinolyl
110
CH.sub.2 O
2-methyl-4-quinolyl
111
CH.sub.2 S
2-methyl-4-quinolyl
112
CH.sub.2 O
2-trichloromethyl-4-quinolyl
113
CH.sub.2 S
2-trichloromethyl-4-quinolyl
114
CH.sub.2 O
2-trifluoromethyl-2-quinolyl
115
CH.sub.2 S
2-trifluoromethyl-2-quinolyl
116
CH.sub.2 O
2-iso-propyl-4-quinolyl
117
CH.sub.2 S
2-iso-propyl-4-quinolyl
118
CH.sub.2 O
2-n-pentyl-4-quinolyl
119
CH.sub.2 S
2-n-pentyl-4-quinolyl
120
CH.sub.2 O
2-phenyl-4-quinolyl
121
CH.sub.2 S
2-phenyl-4-quinolyl
122
CH.sub.2 O
2-methoxycarbonyl-4-quinolyl
123
CH.sub.2 S
2-methoxycarbonyl-4-quinolyl
124
CH.sub.2 O
2,6-dimethyl-4-quinolyl
125
CH.sub.2 S
2,6-dimethyl-4-quinolyl
126
CH.sub.2 O
2-methyl-6-chloro-4-quinolyl
127
CH.sub.2 S
2-methyl-6-chloro-4-quinolyl
128
CH.sub.2 O
2-methyl-6-fluoro-4-quinolyl
129
CH.sub.2 S
2-methyl-6-fluoro-4-quinolyl
130
CH.sub.2 O
8-quinolyl
131
CH.sub.2 S
8-quinolyl
132
CH.sub.2 O
2-methyl-8-quinolyl
133
CH.sub.2 S
2-methyl-8-quinolyl
134
CH.sub.2 O
5,7-dichloro-8-quinolyl
135
CH.sub.2 S
5,7-dichloro-8-quinolyl
136
CH.sub.2 O
4,6-dimethyl-2-pyrimidinyl
137
CH.sub.2 S
4,6-dimethyl-2-pyrimidinyl
138
CH.sub.2 O
4-trifluoromethyl-2-pyrimidinyl
139
CH.sub.2 S
4-trifluoromethyl-2-pyrimidinyl
140
CH.sub.2 O
4,5,6-trimethyl-2-pyrimidinyl
141
CH.sub.2 S
4,5,6-trimethyl-2-pyrimidinyl
142
CH.sub.2 O
4-benzyl-6-methyl-2-pyrimidinyl
143
CH.sub.2 S
4-benzyl-6-methyl-2-pyrimidinyl
144
CH.sub.2 O
4-methyl-6-phenyl-2-pyrimidinyl
145
CH.sub.2 S
4-methyl-6-phenyl-2-pyrimidinyl
146
CH.sub.2 O
4,6-dimethyl-5-chloro-2-pyrimidinyl
147
CH.sub.2 S
4,6-dimethyl-5-chloro-2-pyrimidinyl
148
CH.sub.2 O
2,6-dimethyl-4-pyrimidinyl
149
CH.sub.2 S
2,6-dimethyl-4-pyrimidinyl
150
CH.sub.2 O
2,6-bis-(trifluoromethyl)-4-pyrimidinyl
151
CH.sub.2 S
2,6-bis-(trifluoromethyl)-4-pyrimidinyl
152
CH.sub.2 O
2-chloromethyl-6-methyl-4-pyrimidinyl
153
CH.sub.2 S
2-chloromethyl-6-methyl-4-pyrimidinyl
154
CH.sub.2 O
2-methyl-6-chloromethyl-4-pyrimidinyl
155
CH.sub.2 S
2-methyl-6-chloromethyl-4-pyrimidinyl
156
CH.sub.2 O
2-iso-propyl-6-methyl-4-pyrimidinyl
157
CH.sub.2 S
2-iso-propyl-6-methyl-4-pyrimidinyl
158
CH.sub.2 O
2-iso-propyl-6-chloromethyl-4-pyrimidinyl
159
CH.sub.2 S
2-iso-propyl-6-chloromethyl-4-pyrimidinyl
160
CH.sub.2 O
2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl
161
CH.sub.2 S
2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl
162
CH.sub.2 O
2-cyclo-propyl-6-methyl-4-pyrimidinyl
163
CH.sub.2 S
2-cyclo-propyl-6-methyl-4-pyrimidinyl
164
CH.sub.2 O
2-methyl-6-methoxymethyl-4-pyrimidinyl
165
CH.sub.2 S
2-methyl-6-methoxymethyl-4-pyrimidinyl
166
CH.sub.2 O
2-iso-propyl-6-methoxymethyl-4-pyrimidinyl
167
CH.sub.2 S
2-iso-propyl-6-methoxymethyl-4-pyrimidinyl
168
CH.sub.2 O
2-phenyl-4-pyrimidinyl
169
CH.sub.2 S
2-phenyl-4-pyrimidinyl
170
CH.sub.2 O
3,5-dimethyl-4-pyrimidinyl
171
CH.sub.2 S
3,5-dimethyl-4-pyrimidinyl
172
CH.sub.2 O
2-methylthio-6-trifluoromethyl-4-pyrimidinyl
173
CH.sub.2 S
2-methylthio-6-trifluoromethyl-4-pyrimidinyl
174
CH.sub.2 O
2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl
175
CH.sub.2 S
2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl
176
CH.sub.2 O
2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl
177
CH.sub.2 S
2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl
178
CH.sub.2 O
2-methyl-6-trifluoromethyl-4-pyrimidinyl
179
CH.sub.2 S
2-methyl-6-trifluoromethyl-4-pyrimidinyl
180
CH.sub.2 O
2-n-propyl-6-trifluoromethyl-4-pyrimidinyl
181
CH.sub.2 S
2-n-propyl-6-trifluoromethyl-4-pyrimidinyl
182
CH.sub.2 O
2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl
183
CH.sub.2 S
2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl
184
CH.sub.2 O
2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl
185
CH.sub.2 S
2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl
186
CH.sub.2 O
2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
187
CH.sub.2 S
2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
188
CH.sub.2 O
2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
189
CH.sub.2 S
2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
190
CH.sub.2 O
2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
191
CH.sub.2 S
2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
192
CH.sub.2 O
2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl
193
CH.sub.2 S
2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl
194
CH.sub.2 S
2-pyrimidinyl 62-64
195
CH.sub.2 O
6-cyclopropyl-2-pyridyl
196
CH.sub.2 S
6-cyclopropyl-2-pyridyl
197
CH.sub.2 O
2-pyrazinyl
198
CH.sub.2 S
2-pyrazinyl
199
CH.sub.2 O
6-chloro-2-pyrazinyl
200
CH.sub.2 S
6-chloro-2-pyrazinyl
201
CH.sub.2 O
5-methyl-2-pyrazinyl
202
CH.sub.2 S
5-methyl-2-pyrazinyl
203
CH.sub.2 O
3-pyridazinyl
204
CH.sub.2 S
3-pyridazinyl
205
CH.sub.2 O
5-chloro-3-pyridazinyl
206
CH.sub.2 S
5-chloro-3-pyridazinyl
207
CH.sub.2 O
2-thienyl
208
CH.sub.2 S
2-thienyl
209
CH.sub.2 O
3-thienyl
210
CH.sub.2 S
3-thienyl
211
CH.sub.2 O
4-chloro-3-thienyl
212
CH.sub.2 S
4-chloro-3-thienyl
213
CH.sub.2 O
2-chloro-3-thienyl
214
CH.sub.2 S
2-chloro-3-thienyl
215
CH.sub.2 O
5-chloro-3-thienyl
216
CH.sub.2 S
5-chloro-3-thienyl
217
CH.sub.2 O
2-quinoxalinyl
218
CH.sub.2 S
2-quinoxalinyl
219
CH.sub.2 O
3-methyl-2-quinoxalinyl
220
CH.sub.2 S
3-methyl-2-quinoxalinyl
221
CH.sub.2 O
7,8-dimethyl-2-quinoxalinyl
222
CH.sub.2 S
7,8-dimethyl-2-quinoxalinyl
223
CH.sub.2 O
7,8-dichloro-2-quinoxalinyl
224
CH.sub.2 S
7,8-dichloro-2-quinoxalinyl
225
CH.sub.2 O
7-methyl-2-quinoxalinyl
226
CH.sub.2 S
7-methyl-2-quinoxalinyl
227
CH.sub.2 O
8-methyl-2-quinoxalinyl
›CHCH H · 21 of 24
228
CH.sub.2 S
8-methyl-2-quinoxalinyl
229
CH.sub.2 O
7-methoxy-2-qunioxalinyl
230
CH.sub.2 S
7-methoxy-2-quinoxalinyl
231
CH.sub.2 O
3-phenyl-5-isoxazolyl
232
CH.sub.2 S
3-phenyl-5-isoxazolyl
233
CH.sub.2 O
2-benzoxazolyl
234
CH.sub.2 S
2-benzoxazolyl
235
CH.sub.2 O
2-benzthiazolyl
236
CH.sub.2 S
2-benzthiazolyl
237
CH.sub.2 S
6-methyl-2-benzthiazolyl 86-88
238
CH.sub.2 S
4-chloro-2-benzthiazolyl oil 4.6(S, 2H); 7, 55(S, 1H)
239
CH.sub.2 S
5-chloro-2-benzthiazolyl 131-133
240
CH.sub.2 S
6-chloro-2-benzthiazolyl 86-89
241
CH.sub.2 S
6-ethoxy-2-benzthiazolyl
242
CH.sub.2 S
5-trifluoromethyl-2-benzthiazolyl
oil 4.6(S, 2H); 7.55(S, 1H)
243
CH.sub.2 S
4,8-dimethyl-2-quinolyl
244
CH.sub.2 O
4,8-dimethyl-2-quinolyl
245
CH.sub.2 O
6-iso-butyl-2-pyridyl
246
CH.sub.2 O
3-cyano-6-iso-butyl-2-pyridyl
__________________________________________________________________________
__________________________________________________________________________
##STR47##
No.
A Hetaryl mp NMR: δ (ppm)
__________________________________________________________________________
1 CH.sub.2S
4-pyridyl
2 CH.sub.2O
6-methyl-2-pyridyl oil
3.95(S, 3H); 4.05
(S, 3H); 5.35(S, 2H)
3 CH.sub.2S
6-methyl-2-pyridyl
4 CH.sub.2O
6-ethyl-2-pyridyl
5 CH.sub.2S
6-ethyl-2-pyridyl
6 CH.sub.2O
6-n-propyl-2-pyridyl
7 CH.sub.2S
6-n-propyl-2-pyridyl
8 CH.sub.2O
6-iso-propyl-2-pyridyl
9 CH.sub.2S
6-iso-propyl-2-pyridyl
10 CH.sub.2O
6-n-butyl-2-pyridyl
11 CH.sub.2S
6-n-butyl-2-pyridyl
12 CH.sub.2O
6-tert.-butyl-2-pyridyl
13 CH.sub.2S
6-tert.-butyl-2-pyridyl
14 CH.sub.2O
6-n-pentyl-2-pyridyl
15 CH.sub.2S
6-n-pentyl-2-pyridyl
16 CH.sub.2O
6-n-hexyl-2-pyridyl
17 CH.sub.2S
6-n-hexyl-2-pyridyl
18 CH.sub.2O
6-phenyl-2-pyridyl
19 CH.sub.2S
6-phenyl-2-pyridyl
20 CH.sub.2O
6-benzyl-2-pyridyl
21 CH.sub.2S
6-benzyl-2-pyridyl
22 CH.sub.2S
6-benzyl-2-pyridyl
23 CH.sub.2S
6-trifluoromethyl-2-pyridyl
24 CH.sub.2O
6-methoxy-2-pyridyl
25 CH.sub.2S
6-methoxy-2-pyridyl
26 CH.sub.2O
6-chloro-2-pyridyl
27 CH.sub.2S
6-chloro-2-pyridyl
28 CH.sub.2O
3,6-dimethyl-2-pyridyl
29 CH.sub.2S
3,6-dimethyl-2-pyridyl
30 CH.sub.2O
3,6-diethyl-2-pyridyl
31 CH.sub.2S
3,6-diethyl-2-pyridyl
32 CH.sub.2O
4,6-dimethyl-2-pyridyl
33 CH.sub.2S
4,6-dimethyl-2-pyridyl
34 CH.sub.2O
5,6-dimethyl-2-pyridyl
35 CH.sub.2S
5,6-dimethyl-2-pyridyl
36 CH.sub.2O
4-phenyl-6-methyl-2-pyridyl
37 CH.sub.2S
4-phenyl-6-methyl-2-pyridyl
38 CH.sub.2O
4,6-diphenyl-2-pyridyl
39 CH.sub.2S
4,6-diphenyl-2-pyridyl
40 CH.sub.2O
3,4-dichloro-6-methyl-2-pyridyl
41 CH.sub.2S
3,4-dichloro-6-methyl-2-pyridyl
42 CH.sub.2O
3,4,5-trichloro-6-phenyl-2-pyridyl
43 CH.sub.2S
3,4,5-trichloro-6-phenyl-2-pyridyl
44 CH.sub.2O
4-trifluoromethyl-6-methyl-2-pyridyl
45 CH.sub.2S
4-trifluoromethyl-6-methyl-2-pyridyl
46 CH.sub.2O
3-acetyl-4,6-dimethyl-2-pyridyl
47 CH.sub.2S
3-acetyl-4,6-dimethyl-2-pyridyl
48 CH.sub.2O
3-cyano-6-methyl-2-pyridyl
49 CH.sub.2S
3-cyano-6-methyl-2-pyridyl
50 CH.sub.2O
3-cyano-6-ethyl-2-pyridyl
51 CH.sub.2S
3-cyano-6-ethyl-2-pyridyl
52 CH.sub.2O
3-cyano-6-n-propyl-2-pyridyl
53 CH.sub.2S
3-cyano-6-n-propyl-2-pyridyl
54 CH.sub.2O
3-cyano-6-iso-propyl-2-pyridyl
55 CH.sub.2S
3-cyano-6-iso-propyl-2-pyridyl
56 CH.sub.2O
3-cyano-6-cyclo-propyl-2-pyridyl
57 CH.sub.2S
3-cyano-6-cyclo-propyl-2-pyridyl
58 CH.sub.2O
3-cyano-6-n-butyl-2-pyridyl
59 CH.sub.2S
3-cyano-6-n-butyl-2-pyridyl
60 CH.sub.2O
3-cyano-6-tert.-butyl-2-pyridyl
61 CH.sub.2S
3-cyano-6-tert.-butyl-2-pyridyl
62 CH.sub.2O
3-cyano-6-cyclo-hexyl-2-pyridyl
63 CH.sub.2S
3-cyano-6-cyclo-hexyl-2-pyridyl
64 CH.sub.2O
3-cyano-6-phenyl-2-pyridyl
65 CH.sub.2S
3-cyano-6-phenyl-2-pyridyl
66 CH.sub.2O
3-methyloxycarbonyl-6-iso-propyl-2-pyridyl
67 CH.sub.2S
3-methyloxycarbonyl-6-iso-propyl-2-pyridyl
68 CH.sub.2O
3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl
69 CH.sub.2S
3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl
70 CH.sub.2O
3-cyano-4,6-dimethyl-2-pyridyl
71 CH.sub.2S
3-cyano-4,6-dimethyl-2-pyridyl
72 CH.sub.2O
3,5,6-trichloro-2-pyridyl
73 CH.sub.2S
3,5,6-trichloro-2-pyridyl
74 CH.sub.2O
5-trifluoromethyl-2-pyridyl
75 CH.sub.2S
5-trifluoromethyl-2-pyridyl
76 CH.sub.2O
3-chloro-5-trifluoromethyl-2-pyridyl
77 CH.sub.2S
3-chloro-5-trifluoromethyl-2-pyridyl
78 CH.sub.2O
2-quinolyl
79 CH.sub.2S
2-quinolyl
80 CH.sub.2O
3-methyl-2-quinolyl
81 CH.sub.2S
3-methyl-2-quinolyl
82 CH.sub.2O
4-methyl-2-quinolyl
83 CH.sub.2S
4-methyl-2-quinolyl
84 CH.sub.2O
4-ethyl-2-quinolyl
85 CH.sub.2S
4-ethyl-2-quinolyl
86 CH.sub.2O
4-phenyl-2-quinolyl
87 CH.sub.2S
4-phenyl-2-quinolyl
88 CH.sub.2O
6-methyl-2-quinolyl
89 CH.sub.2S
6-methyl-2-quinolyl
90 CH.sub.2O
6-chloro-2-quinolyl
91 CH.sub.2S
6-chloro-2-quinolyl
92 CH.sub.2O
8-methyl-2-quinolyl
93 CH.sub.2S
8-methyl-2-quinolyl
94 CH.sub.2O
8-chloro-2-quinolyl
95 CH.sub.2S
8-chloro-2-quinolyl
96 CH.sub.2O
4-ethoxycarbonyl-2-quinolyl
97 CH.sub.2S
4-ethoxycarbonyl-2-quinolyl
98 CH.sub.2O
3,4-dimethyl-2-quinolyl
99 CH.sub.2S
3,4-dimethyl-2-quinolyl
100
CH.sub.2O
4-methyl-8-methoxy-2-quinolyl
101
CH.sub.2S
4-methyl-8-methoxy-2-quinolyl
102
CH.sub.2O
4-phenyl-8-ethoxy-2-quinolyl
103
CH.sub.2S
4-phenyl-8-ethoxy-2-quinolyl
104
CH.sub.2O
4-methyl-8-chloro-2-quinolyl
105
CH.sub.2S
4-methyl-8-chloro-2-quinolyl
106
CH.sub.2O
4-methyl-8-fluoro-2-quinolyl
107
CH.sub.2S
4-methyl-8-fluoro-2-quinolyl
108
CH.sub.2O
4-quinolyl
109
CH.sub.2S
4-quinolyl
110
CH.sub.2O
2-methyl-4-quinolyl
111
CH.sub.2S
2-methyl-4-quinolyl
112
CH.sub.2O
2-trichloromethyl-4-quinolyl
113
CH.sub.2S
2-trichloromethyl-4-quinolyl
114
CH.sub.2O
2-trichloromethyl-2-quinolyl
115
CH.sub.2S
2-trichloromethyl-2-quinolyl
116
CH.sub.2O
2-iso-propyl-4-quinolyl
117
CH.sub.2S
2-iso-propyl-4-quinolyl
118
CH.sub.2O
2-n-pentyl-4-quinolyl
119
CH.sub.2S
2-n-pentyl-4-quinolyl
120
CH.sub.2O
2-phenyl-4-quinolyl
121
CH.sub.2S
2-phenyl-4-quinolyl
122
CH.sub.2O
2-methoxycarbonyl-4-quinolyl
123
CH.sub.2S
2-methoxycarbonyl-4-quinolyl
124
CH.sub.2O
2,6-dimethyl-4-quinolyl
125
CH.sub.2S
2,6-dimethyl-4-quinolyl
126
CH.sub.2O
2-methyl-6-chloro-4-quinolyl
127
CH.sub.2S
2-methyl-6-chloro-4-quinolyl
128
CH.sub.2O
2-methyl-6-fluoro-4-quinolyl
129
CH.sub.2S
2-methyl-6-fluoro-4-quinolyl
130
CH.sub.2O
8-quinolyl
131
CH.sub.2S
8-quinolyl
132
CH.sub.2O
2-methyl-8-quinolyl
133
CH.sub.2S
2-methyl-8-quinolyl
134
CH.sub.2O
5,7-dichloro-8-quinolyl
135
CH.sub.2S
5,7-dichloro-8-quinolyl
136
CH.sub.2O
4,6-dimethyl-2-pyrimidinyl
137
CH.sub.2S
4,6-dimethyl-2-pyrimidinyl
138
CH.sub.2O
4-trifluoromethyl-2-pyrimidinyl
›CHCH H · 22 of 24
139
CH.sub.2S
4-trifluoromethyl-2-pyrimidinyl
140
CH.sub.2O
4,5,6-trimethyl-2-pyrimidinyl
141
CH.sub.2S
4,5,6-trimethyl-2-pyrimidinyl
142
CH.sub.2O
4-benzyl-6-methyl-2-pyrimidinyl
143
CH.sub.2S
4-benzyl-6-methyl-2-pyrimidinyl
144
CH.sub.2O
4-methyl-6-phenyl-2-pyrimidinyl
145
CH.sub.2S
4-methyl-6-phenyl-2-pyrimidinyl
146
CH.sub.2O
4,5-dimethyl-5-chloro-2-pyrimidinyl
147
CH.sub.2S
4,5-dimethyl-5-chloro-2-pyrimidinyl
148
CH.sub.2O
2,6-dimethyl-4-pyrimidinyl
149
CH.sub.2S
2,6-dimethyl-4-pyrimidinyl
150
CH.sub.2O
2,6-bis-(trifluoromethyl)-4-pyrimidinyl
151
CH.sub.2S
2,6-bis-(trifluoromethyl)-4-pyrimidinyl
152
CH.sub.2O
2-chloromethyl-6-methyl-4-pyrimidinyl
153
CH.sub.2S
2-chloromethyl-6-methyl-4-pyrimidinyl
154
CH.sub.2O
2-methyl-6-chloromethyl-4-pyrimidinyl
155
CH.sub.2S
2-methyl-6-chloromethyl-4-pyrimidinyl
156
CH.sub.2O
2-iso-propyl-6-methyl-4-pyrimidinyl
157
CH.sub.2S
2-iso-propyl-6-methyl-4-pyrimidinyl
158
CH.sub.2O
2-iso-propyl-6-chloromethyl-4-pyrimidinyl
159
CH.sub.2S
2-iso-propyl-6-chloromethyl-4-pyrimidinyl
160
CH.sub.2O
2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl
161
CH.sub.2S
2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl
162
CH.sub.2O
2-cyclo-propyl-6-methyl-4-pyrimidinyl
163
CH.sub.2S
2-cyclo-propyl-6-methyl-4-pyrimidinyl
164
CH.sub.2O
2-methyl-6-methoxymethyl-4-pyrimidinyl
165
CH.sub.2S
2-methyl-6-methoxymethyl-4-pyrimidinyl
166
CH.sub.2O
2-iso-propyl-6-methoxymethyl-4-pyrimidinyl
167
CH.sub.2S
2-iso-propyl-6-methoxymethyl-4-pyrimidinyl
168
CH.sub.2O
2-phenyl-4-pyrimidinyl
169
CH.sub.2S
2-phenyl-4-pyrimidinyl
170
CH.sub.2O
3,5-dimethyl-4-pyrimidinyl
171
CH.sub.2S
3,5-dimethyl-4-pyrimidinyl
172
CH.sub.2O
2-methylthio-6-trifluoromethyl-4-pyrimidinyl
173
CH.sub.2S
2-methylthio-6-trifluoromethyl-4-pyrimidinyl
174
CH.sub.2O
2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl
175
CH.sub.2S
2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl
176
CH.sub.2O
2-methylthio-5-n-octyl-6-trifluoromethyl-4-pyrimidinyl
177
CH.sub.2S
2-methylthio-5-n-octyl-6-trifluoromethyl-4-pyrimidinyl
178
CH.sub.2O
2-methyl-6-trifluoromethyl-4-pyrimidinyl
179
CH.sub.2S
2-methyl-6-trifluoromethyl-4-pyrimidinyl
180
CH.sub.2O
2-n-propyl-6-trifluoromethyl-4-pyrimidinyl
181
CH.sub.2S
2-n-propyl-6-trifluoromethyl-4-pyrimidinyl
182
CH.sub.2O
2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl
183
CH.sub.2S
2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl
184
CH.sub.2O
2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl
185
CH.sub.2S
2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl
186
CH.sub.2O
2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
187
CH.sub.2S
2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
188
CH.sub.2O
2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
189
CH.sub.2S
2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
190
CH.sub.2O
2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
191
CH.sub.2S
2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
192
CH.sub.2O
2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
193
CH.sub.2S
2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
194
CH.sub.2S
2-pyrimidinyl
195
CH.sub.2O
6-cyclopropyl-2-pyridyl
196
CH.sub.2S
6-cyclopropyl-2-pyridyl
197
CH.sub.2O
2-pyrazinyl
198
CH.sub.2S
2-pyrazinyl
199
CH.sub.2O
6-chloro-2-pyrazinyl
200
CH.sub.2S
6-chloro-2-pyrazinyl
201
CH.sub.2O
5-methyl-2-pyrazinyl
202
CH.sub.2S
5-methyl-2-pyrazinyl
203
CH.sub.2O
3-pyridazinyl
204
CH.sub.2S
3-pyridazinyl
205
CH.sub.2O
5-chloro-3-pyridazinyl
206
CH.sub.2S
5-chloro-3-pyridazinyl
207
CH.sub.2O
2-thienyl
208
CH.sub.2S
2-thienyl
209
CH.sub.2O
3-thienyl
210
CH.sub.2S
3-thienyl
211
CH.sub.2O
4-chloro-3-thienyl
212
CH.sub.2S
4-chloro-3-thienyl
213
CH.sub.2O
2-chloro-3-thienyl
214
CH.sub.2S
2-chloro-3-thienyl
215
CH.sub.2O
5-chloro-3-thienyl
216
CH.sub.2S
5-chloro-3-thienyl
217
CH.sub.2O
2-quinoxalinyl
218
CH.sub.2S
2-quinoxalinyl
219
CH.sub.2O
3-methyl-2-quinoxalinyl
220
CH.sub.2S
3-methyl-2-quinoxalinyl
221
CH.sub.2O
7,8-dimethyl-2-quinoxalinyl
222
CH.sub.2S
7,8-dimethyl-2-quinoxalinyl
223
CH.sub.2O
7,8-dichloro-2-quinoxalinyl
224
CH.sub.2S
7,8-dichloro-2-quinoxalinyl
225
CH.sub.2O
7-methyl-2-quinoxalinyl
226
CH.sub.2S
7-methyl-2-quinoxalinyl
227
CH.sub.2O
8-methyl-2-quinoxalinyl
228
CH.sub.2S
8-methyl-2-quinoxalinyl
229
CH.sub.2O
7-methoxy-2-quinoxalinyl
230
CH.sub.2S
7-methoxy-2-quinoxalinyl
231
CH.sub.2O
3-phenyl-5-isoxazolyl
232
CH.sub.2S
3-phenyl-5-isoxazolyl
233
CH.sub.2O
2-benzoxazolyl
234
CH.sub.2S
2-benzoxazolyl
235
CH.sub.2O
2-benzthiazolyl
236
CH.sub.2S
2-benzthiazolyl
237
CH.sub.2S
6-methyl-2-benzthiazolyl (non-polar isomer)
oil
3.9(S, 3H); 4.0(S, 3H);
4.55(S, 2H)
238
CH.sub.2S
4-chloro-2-benzthiazolyl
239
CH.sub.2S
5-chloro-2-benzthiazolyl
240
CH.sub.2S
6-chloro-2-benzthiazolyl
241
CH.sub.2S
6-ethoxy-2-benzthiazolyl
242
CH.sub.2S
5-trifluoromethyl-2-benzthiazolyl
243
CH.sub.2S
4,8-dimethyl-2-quinolyl
244
CH.sub.2O
4,8-dimethyl-2-quinolyl
245
CH.sub.2O
6-iso-butyl-2-pyridyl
246
CH.sub.2O
3-cyano-6-iso-butyl-2-pyridyl
__________________________________________________________________________
__________________________________________________________________________
##STR48##
No.
A Hetaryl mp
NMR: δ (ppm)
__________________________________________________________________________
1 CH.sub.2 S
4-pyridyl
2 CH.sub.2 O
6-methyl-2-pyridyl oil
3.95(S, 3H); 4.05
(S, 3H); 5.35(S, 2H)
3 CH.sub.2 S
6-methy-2-pyridyl
4 CH.sub.2 O
6-ethyl-2-pyridyl
5 CH.sub.2 S
6-ethyl-2-pyridyl
6 CH.sub.2 O
6-n-propyl-2-pyridyl
7 CH.sub.2 S
6-n-propyl-2-pyridyl
8 CH.sub.2 O
6-iso-propyl-2-pyridyl
9 CH.sub.2 S
6-iso-propyl-2-pyridyl
10
CH.sub.2 O
6-n-butyl-2-pyridyl
11
Ch.sub.2 S
6-n-butyl-2-pyridyl
12
CH.sub.2 O
6-tert.-butyl-2-pyridyl
13
CH.sub.2 S
6-tert.-butyl-2-pyridyl
14
CH.sub.2 O
6-n-pentyl-2-pyridyl
15
CH.sub.2 S
6-n-pentyl-2-pyridyl
16
CH.sub.2 O
6-n-hexyl-2-pyridyl
17
CH.sub.2 S
6-n-hexyl-2-pyridyl
18
CH.sub.2 O
6-phenyl-2-pyridyl
19
CH.sub.2 S
6-phenyl-2-pyridyl
20
CH.sub.2 O
6-benzyl-2-pyridyl
21
CH.sub.2 S
6-benzyl-2-pyridyl
22
CH.sub.2 S
6-benzyl-2-pyridyl
23
CH.sub.2 S
6-trifluoromethyl-2-pyridyl
24
CH.sub.2 O
6-methoxy-2-pyridyl
25
CH.sub.2 S
6-methoxy-2-pyridyl
26
CH.sub.2 O
6-chloro-2-pyridyl
27
CH.sub.2 S
6-chloro-2-pyridyl
28
CH.sub.2 O
3,6-dimethyl-2-pyridyl
29
CH.sub.2 S
3,6-dimethyl-2-pyridyl
30
CH.sub.2 O
3,6-diethyl-2-pyridyl
31
CH.sub.2 S
3,6-diethyl-2-pyridyl
32
CH.sub.2 O
4,6-dimethyl-2-pyridyl
33
CH.sub.2 S
4,6-dimethyl-2-pyridyl
34
CH.sub.2 O
5,6-dimethyl-2-pyridyl
35
CH.sub.2 S
5,6-dimethyl-2-pyridyl
36
CH.sub.2 O
›CHCH H · 23 of 24
4-phenyl-6-methyl-2-pyridyl
37
CH.sub.2 S
4-phenyl-6-methyl-2-pyridyl
38
CH.sub.2 O
4,6-diphenyl-2-pyridyl
39
CH.sub.2 S
4,6-diphenyl-2-pyridyl
40
CH.sub.2 O
3,4-dichloro-6-methyl-2-pyridyl
41
CH.sub.2 S
3,4-dichloro-6-methyl-2-pyridyl
42
CH.sub.2 O
3,4,5-trichloro-6-phenyl-2-pyridyl
43
CH.sub.2 S
3,4,5-trichloro-6-phenyl-2-pyridyl
44
CH.sub.2 O
4-trifluoromethyl-6-methyl-2-pyridyl
45
CH.sub.2 S
4-trifluoromethyl-6-methyl-2-pyridyl
46
CH.sub.2 O
3-acetyl-4,6-dimethyl-2-pyridyl
47
CH.sub.2 S
3-acetyl-4,6-dimethyl-2-pyridyl
48
CH.sub.2 O
3-cyano-6-methyl-2-pyridyl
49
CH.sub.2 S
3-cyano-6-methyl-2-pyridyl
50
CH.sub.2 O
3-cyano-6-ethyl-2-pyridyl
51
CH.sub.2 S
3-cyano-6-ethyl-2-pyridyl
52
CH.sub.2 O
3-cyano-6-n-propyl-2-pyridyl
53
CH.sub.2 S
3-cyano-6-n-propyl-2-pyridyl
54
CH.sub.2 O
3-cyano-6-iso-propyl-2-pyridyl
55
CH.sub.2 S
3-cyano-6-iso-propyl-2-pyridyl
56
CH.sub.2 O
3-cyano-6-cyclo-propyl-2-pyridyl
57
CH.sub.2 S
3-cyano-6-cyclo-propyl-2-pyridyl
58
CH.sub.2 O
3-cyano-6-n-butyl-2-pyridyl
59
CH.sub.2 S
3-cyano-6-n-butyl-2-pyridyl
60
CH.sub.2 O
3-cyano-6-tert.-butyl-2-pyridyl
61
CH.sub.2 S
3-cyano-6-tert.-butyl-2-pyridyl
62
CH.sub.2 O
3-cyano-6-cyclo-hexyl-2-pyridyl
63
CH.sub.2 S
3-cyano-6-cyclo-hexyl-2-pyridyl
64
CH.sub.2 O
3-cyano-6-phenyl-2-pyridyl
65
CH.sub.2 S
3-cyano-6-phenyl-2-pyridyl
66
CH.sub.2 O
3-methyloxycarbonyl-6-iso-propyl-2-pyridyl
67
CH.sub.2 S
3-methyloxycarbonyl-6-iso-propyl-2-pyridyl
68
CH.sub.2 O
3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl
69
CH.sub.2 S
3-ethyloxycarbonyl-6-iso-propyl-2-pyridyl
70
CH.sub.2 O
3-cyano-4,6-dimethyl-2-pyridyl
71
CH.sub.2 S
3-cyano-4,6-dimethyl-2-pyridyl
72
CH.sub.2 O
3,5,6-trichloro-2-pyridyl
73
CH.sub.2 S
3,5,6-trichloro-2-pyridyl
74
CH.sub.2 O
5-trifluoromethyl-2-pyridyl
75
CH.sub.2 S
5-trifluoromethyl-2-pyridyl
76
CH.sub.2 O
3-chloro-5-trifluoromethyl-2-pyridyl
77
CH.sub.2 S
3-chloro-5-trifluoromethyl-2-pyridyl
78
CH.sub.2 O
2-quinolyl
79
CH.sub.2 S
2-quinolyl
80
CH.sub.2 O
3-methyl-2-quinolyl
81
CH.sub.2 S
3-methyl-2-quinolyl
82
CH.sub.2 O
4-methyl-2-quinolyl
83
CH.sub.2 S
4-methyl-2-quinolyl
84
CH.sub.2 O
4-ethyl-2-quinolyl
85
CH.sub.2 S
4-ethyl-2-quinolyl
86
CH.sub.2 O
4-phenyl-2-quinolyl
87
CH.sub.2 S
4-phenyl-2-quinolyl
88
CH.sub.2 O
6-methyl-2-quinolyl
89
CH.sub.2 S
6-methyl-2-quinolyl
90
CH.sub.2 O
6-chloro-2-quinolyl
91
CH.sub.2 S
6-chloro-2-quinolyl
92
CH.sub.2 O
8-methyl-2-quinolyl
93
CH.sub.2 S
8-methyl-2-quinolyl
94
CH.sub.2 O
8-chloro-2-quinolyl
95
CH.sub.2 S
8-chloro-2-quinolyl
96
CH.sub.2 O
4-Ethoxycarbonyl-2-quinolyl
97
CH.sub.2 S
4-Ethoxycarbonyl-2-quinolyl
98
CH.sub.2 O
3,4-dimethyl-2-quinolyl
99
CH.sub.2 S
3,4-dimethyl-2-quinolyl
100
CH.sub.2 O
4-methyl-8-methoxy-2-quinolyl
101
CH.sub.2 S
4-methyl-8-methoxy-2-quinolyl
102
CH.sub.2 O
4-phenyl-8-ethoxy-2-quinolyl
103
CH.sub.2 S
4-phenyl-8-ethoxy-2-quinolyl
104
CH.sub.2 O
4-methyl-8-chloro-2-quinolyl
105
CH.sub.2 S
4-methyl-8-chloro-2-quinolyl
106
CH.sub.2 O
4-methyl-8-fluoro-2-quinolyl
107
CH.sub.2 S
4-methyl-8-fluoro-2-quinolyl
108
CH.sub.2 O
4-quinolyl
109
CH.sub.2 S
4-quinolyl
110
CH.sub.2 O
2-methyl-4-quinolyl
111
CH.sub.2 S
2-methyl-4-quinolyl
112
CH.sub.2 O
2-trichloromethyl-4-quinolyl
113
CH.sub.2 S
2-trichloromethyl-4-quinolyl
114
CH.sub.2 O
2-trifluoromethyl-2-quinolyl
115
CH.sub.2 S
2-trifluoromethyl-2-quinolyl
116
CH.sub.2 O
2-iso-propyl-4-quinolyl
117
CH.sub.2 S
2-iso-propyl-4-quinolyl
118
CH.sub.2 O
2-n-pentyl-4-quinolyl
119
CH.sub.2 S
2-n-pentyl-4-quinolyl
120
CH.sub.2 O
2-phenyl-4-quinolyl
121
CH.sub.2 S
2-phenyl-4-quinolyl
122
CH.sub.2 O
2-methoxycarbonyl-4-quinolyl
123
CH.sub.2 S
2-methoxycarbonyl-4-quinolyl
124
CH.sub.2 O
2,6-dimethyl-4-quinolyl
125
CH.sub.2 S
2,6-dimethyl-4-quinolyl
126
CH.sub.2 O
2-methyl-6-chloro-4-quinolyl
127
CH.sub.2 S
2-methyl-6-chloro-4-quinolyl
128
CH.sub.2 O
2-methyl-6-fluoro-4-quinolyl
129
CH.sub.2 S
2-methyl-6-fluoro-4-quinolyl
130
CH.sub.2 O
8-quinolyl
131
CH.sub.2 S
8-quinolyl
132
CH.sub.2 O
2-methyl-8-quinolyl
133
CH.sub.2 S
2-methyl-8-quinolyl
134
CH.sub.2 O
5,7-dichloro-8-quinolyl
135
CH.sub.2 S
5,7-dichloro-8-quinolyl
136
CH.sub.2 O
4,6-dimethyl-2-pyrimidinyl
137
CH.sub.2 S
4,6-dimethyl-2-pyrimidinyl
138
CH.sub.2 O
4-trifluoromethyl-2-pyrimidinyl
139
CH.sub.2 S
4-trifluoromethyl-2-pyrimidinyl
140
CH.sub.2 O
4,5,6-trimethyl-2-pyrimidinyl
141
CH.sub.2 S
4,5,6-trimethyl-2-pyrimidinyl
142
CH.sub.2 O
4-benzyl-6-methyl-2-pyrimidinyl
143
CH.sub.2 S
4-benzyl-6-methyl-2-pyrimidinyl
144
CH.sub.2 O
4-methyl-6-phenyl-2-pyrimidinyl
145
CH.sub.2 S
4-methyl-6-phenyl-2-pyrimidinyl
146
CH.sub.2 O
4,6-dimethyl-5-chloro-2-pyrimidinyl
147
CH.sub.2 S
4,6-dimethyl-5-chloro-2-pyrimidinyl
148
CH.sub.2 O
2,6-dimethyl-4-pyrimidinyl
149
CH.sub.2 S
2,6-dimethyl-4-pyrimidinyl
150
CH.sub.2 O
2,6-bis-(trifluoromethyl)-4-pyrimidinyl
151
CH.sub.2 S
2,6-bis-(trifluoromethyl)-4-pyrimidinyl
152
CH.sub.2 O
2-chloromethyl-6-methyl-4-pyrimidinyl
153
CH.sub.2 S
2-chloromethyl-6-methyl-4-pyrimidinyl
154
CH.sub.2 O
2-methyl-6-chloromethyl-4-pyrimidinyl
155
CH.sub.2 S
2-methyl-6-chloromethyl-4-pyrimidinyl
156
CH.sub.2 O
2-iso-propyl-6-methyl-4-pyrimidinyl
157
CH.sub.2 S
2-iso-propyl-6-methyl-4-pyrimidinyl
158
CH.sub.2 O
2-iso-propyl-6-chloromethyl-4-pyrimidinyl
159
CH.sub.2 S
2-iso-propyl-6-chloromethyl-4-pyrimidinyl
160
CH.sub.2 O
2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl
161
CH.sub.2 S
2-cyclo-propyl-6-chloromethyl-4-pyrimidinyl
162
CH.sub.2 O
2-cyclo-propyl-6-methyl-4-pyrimidinyl
163
CH.sub.2 S
2-cyclo-propyl-6-methyl-4-pyrimidinyl
164
CH.sub.2 O
2-methyl-6-methoxymethyl-4-pyrimidinyl
165
CH.sub.2 S
2-methyl-6-methoxymethyl-4-pyrimidinyl
166
CH.sub.2 O
2-iso-propyl-6-methoxymethyl-4-pyrimidinyl
167
CH.sub.2 S
2-iso-propyl-6-methoxymethyl-4-pyrimidinyl
168
CH.sub.2 O
2-phenyl-4-pyrimidinyl
169
CH.sub.2 S
2-phenyl-4-pyrimidinyl
170
CH.sub.2 O
3,5-dimethyl-4-pyrimidinyl
171
CH.sub.2 S
3,5-dimethyl-4-pyrimidinyl
172
CH.sub.2 O
2-methylthio-6-trifluoromethyl-4-pyrimidinyl
173
CH.sub.2 S
2-methylthio-6-trifluoromethyl-4-pyrimidinyl
174
CH.sub.2 O
2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl
175
CH.sub.2 S
2-methylthio-5-chloro-6-trifluoromethyl-4-pyrimidinyl
176
CH.sub.2 O
2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl
177
CH.sub.2 S
2-methylthio-5-n-octyl-6-methyl-4-pyrimidinyl
178
CH.sub.2 O
2-methyl-6-trifluoromethyl-4-pyrimidinyl
179
CH.sub.2 S
2-methyl-6-trifluoromethyl-4-pyrimidinyl
180
CH.sub.2 O
2-n-propyl-6-trifluoromethyl-4-pyrimidinyl
181
CH.sub.2 S
2-n-propyl-6-trifluoromethyl-4-pyrimidinyl
›CHCH H · 24 of 24
182
CH.sub.2 O
2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl
183
CH.sub.2 S
2-iso-propyl-6-trifluoromethyl-4-pyrimidinyl
184
CH.sub.2 O
2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl
185
CH.sub.2 S
2-tert.-butyl-6-trifluoromethyl-4-pyrimidinyl
186
CH.sub.2 O
2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
187
CH.sub.2 S
2-methyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
188
CH.sub.2 O
2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
189
CH.sub.2 S
2-n-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
190
CH.sub.2 O
2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
191
CH.sub.2 S
2-iso-propyl-5-chloro-6-trifluoromethyl-4-pyrimidinyl
192
CH.sub.2 O
2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl
193
CH.sub.2 S
2-tert.-butyl-5-chloro-6-trifluoromethyl-4-pyrimidininyl
194
CH.sub.2 S
2-pyrimidinyl
195
CH.sub.2 O
6-cyclopropyl-2-pyridyl
196
CH.sub.2 S
6-cyclopropyl-2-pyridyl
197
CH.sub.2 O
2-pyrizinyl
198
CH.sub.2 S
2-pyrazinyl
199
CH.sub.2 O
6-chloro-2-pyrazinyl
200
CH.sub.2 S
6-chloro-2-pyrazinyl
201
CH.sub.2 O
5-methyl-2-pyrazinyl
202
CH.sub.2 S
5-methyl-2-pyrazinyl
203
CH.sub.2 O
3-pyridazinyl
204
CH.sub.2 S
3-pyridazinyl
205
CH.sub.2 O
5-chloro-3-pyridazinyl
206
CH.sub.2 S
5-chloro-3-pyridazinyl
207
CH.sub.2 O
2-thienyl
208
CH.sub.2 S
2-thienyl
209
CH.sub.2 O
3-thienyl
210
CH.sub.2 S
3-thienyl
211
CH.sub.2 O
4-chloro-3-thienyl
212
CH.sub.2 S
4-chloro-3-thienyl
213
CH.sub.2 O
2-chloro-3-thienyl
214
CH.sub.2 S
2-chloro-3-thienyl
215
CH.sub.2 O
5-chloro-3-thienyl
216
CH.sub.2 S
5-chloro-3-thienyl
217
CH.sub.2 O
2-quinoxalinyl
218
CH.sub.2 S
2-quinoxalinyl
219
CH.sub.2 O
3-methyl-2-quinxalinyl
220
CH.sub.2 S
3-methyl-2-quinxalinyl
221
CH.sub.2 O
7,8-dimethyl-2-quinoxalinyl
222
CH.sub.2 S
7,8-dimethyl-2-quinoxalinyl
223
CH.sub.2 O
7,8-dichloro-2-quinoxalinyl
224
CH.sub.2 S
7,8-dichloro-2-quinoxalinyl
225
CH.sub.2 O
7-methyl-2-quinoxalinyl
226
CH.sub.2 S
7-methyl-2-quinoxalinyl
227
CH.sub.2 O
8-methyl-2-quinoxalinyl
228
CH.sub.2 S
8-methyl-2-quinoxalinyl
229
CH.sub.2 O
7-methoxy-2-quinoxalinyl
230
CH.sub.2 S
7-methoxy-2-quinoxalinyl
231
CH.sub.2 O
3-phenyl-5-isoxazolyl
232
CH.sub.2 S
3-phenyl-5-isoxazolyl
233
CH.sub.2 O
2-benzoxazolyl
234
CH.sub.2 S
2-benzoxazolyl
235
CH.sub.2 O
2-benzthiazolyl
236
CH.sub.2 S
2-benzthiazolyl
237
CH.sub.2 S
6-methyl-2-benzthiazolyl (non-polar isomer)
oil
3.9(S, 3H); 4.0(S, 3H);
4, 55(S, 2H)
238
CH.sub.2 S
4-chloro-2-benzthiazolyl
239
CH.sub.2 S
5-chloro-2-benzthiazolyl
240
CH.sub.2 S
6-chloro-2-benzthiazolyl
241
CH.sub.2 S
6-Ethoxy-2-benzthiazolyl
242
CH.sub.2 S
5-trifluoromethyl-2-benzthiazolyl
243
CH.sub.2 S
4,8-dimethyl-2-quinolyl
244
CH.sub.2 O
4,8-dimethyl-2-quinolyl
245
CH.sub.2 O
6-iso-butyl-2-pyridyl
246
CH.sub.2 O
3-cyano-6-iso-butyl-2-pyridyl
__________________________________________________________________________
__________________________________________________________________________
##STR49##
No.
Z.sup.1
Z.sup.2
U A mp NMR
__________________________________________________________________________
1 2-OCH.sub.3
H HCOCH.sub.3
CH.sub.2 CH.sub.2
2 2-OCH.sub.3
H HCOCH.sub.3
›CHCH
3 2-OCH.sub.3
H HCOCH.sub.3
CH.sub.2 O
4 2-OCH.sub.3
H HCOCH.sub.3
CH.sub.2 OCO
5 2-OCH.sub.3
H NOCH.sub.3
CH.sub.2 CH.sub.2
6 2-OCH.sub.3
H NOCH.sub.3
›CHCH
7 2-OCH.sub.3
H NOCH.sub.3
CH.sub.2 O
8 2-OCH.sub.3
H NOCH.sub.3
CH.sub.2 OCO
9 2-OCH.sub.3
H CHCH.sub.3
CH.sub.2 CH.sub.2
10 2-OCH.sub.3
H CHCH.sub.3
›CHCH
11 2-OCH.sub.3
H CHCH.sub.3
CH.sub.2 O
12 2-OCH.sub.3
H CHCH.sub.3
CH.sub.2 OCO
13 4-OCH.sub.3
H HCOCH.sub.3
CH.sub.2 CH.sub. 2
14 4-OCH.sub.3
H HCOCH.sub.3
›CHCH
15 4-OCH.sub.3
H HCOCH.sub.3
CH.sub.2 O
16 4-OCH.sub.3
H HCOCH.sub.3
CH.sub.2 OCO
17 4-OCH.sub.3
H NOCH.sub.3
CH.sub.2 CH.sub.2
18 4-OCH.sub.3
H NOCH.sub.3
›CHCH
19 4-OCH.sub.3
H NOCH.sub.3
CH.sub.2 O
20 4-OCH.sub.3
H NOCH.sub.3
CH.sub.2 OCO
21 4-OCH.sub.3
H CHCH.sub.3
CH.sub.2 CH.sub.2
22 4-OCH.sub.3
H CHCH.sub.3
›CHCH
23 4-OCH.sub.3
H CHCH.sub.3
CH.sub.2 O
24 4-OCH.sub.3
H CHCH.sub.3
CH.sub.2 OCO
25 6-N(CH.sub.3).sub.2
H HCOCH.sub.3
CH.sub.2 CH.sub.2
26 6-N(CH.sub.3).sub.2
H HCOCH.sub.3
›CHCH
27 6-N(CH.sub.3).sub.2
H HCOCH.sub.3
CH.sub.2 O
28 6-N(CH.sub.3).sub.2
H HCOCH.sub.3
CH.sub.2 OCO
29 6-N(CH.sub.3).sub.2
H NOCH.sub.3
CH.sub.2 CH.sub.2
30 6-N(CH.sub.3).sub.2
H NOCH.sub.3
›CHCH
31 6-N(CH.sub.3).sub.2
H NOCH.sub.3
CH.sub.2 O
32 6-N(CH.sub.3).sub.2
H NOCH.sub. 3
CH.sub.2 O
33 6-N(CH.sub.3).sub.2
H CHCH.sub.3
CH.sub.2 CH.sub.2
34 6-N(CH.sub.3).sub.2
H CHCH.sub.3
›CHCH
35 6-N(CH.sub.3).sub.2
H CHCH.sub.3
CH.sub.2 O
36 6-N(CH.sub.3).sub.2
H CHCH.sub.3
CH.sub.2 OCO
37 5-NO.sub.2
6-OCH.sub.3
HCOCH.sub.3
CH.sub.2 CH.sub.2
38 5-NO.sub.2
6-OCH.sub.3
HCOCH.sub.3
›CHCH
39 5-NO.sub.2
6-OCH.sub.3
HCOCH.sub.3
CH.sub.2 O
40 5-NO.sub.2
6-OCH.sub.3
HCOCH.sub.3
CH.sub.2 OCO
41 5-NO.sub.2
6-OCH.sub.3
NOCH.sub.3
CH.sub.2 CH.sub.2
42 5-NO.sub.2
6-OCH.sub.3
NOCH.sub.3
›CHCH
43 5-NO.sub.2
6-OCH.sub.3
NOCH.sub.3
CH.sub.2 O
44 5-NO.sub.2
6-OCH.sub.3
NOCH.sub.3
CH.sub.2 OCO
45 5-NO.sub.2
6-OCH.sub.3
CHCH.sub.3
CH.sub.2 CH.sub.2
46 5-NO.sub.2
6-OCH.sub.3
CHCH.sub.3
›CHCH · 1 of 3
47 5-NO.sub.2
6-OCH.sub.3
CHCH.sub.3
CH.sub.2 O
48 5-NO.sub.2
6-OCH.sub.3
CHCH.sub.3
CH.sub.2 OCO
49 5-NO.sub.2
H HCOCH.sub.3
OCH.sub.2
50 5-NO.sub.2
H NOCH.sub.3
OCH.sub.2
51 5-NO.sub.2
H CHCH.sub.3
OCH.sub.2
52 4-NO.sub.2
H HCOCH.sub.3
OCH.sub.2
53 4-NO.sub.2
H NOCH.sub.3
OCH.sub.2
54 4-NO.sub.2
H CHCH.sub.3
OCH.sub.2
55 2-CO.sub.2 CH.sub.3
H HCOCH.sub.3
OCH.sub.2
56 2-CO.sub.2 CH.sub.3
H NOCH.sub.3
OCH.sub.2
57 2-CO.sub.2 CH.sub.3
H CHCH.sub.3
OCH.sub.2
58 4-OCH.sub.3
H HCOCH.sub.3
OCH.sub.2
59 4-OCH.sub.3
H NOCH.sub.3
OCH.sub.2
60 4-OCH.sub.3
H CHCH.sub.3
OCH.sub.2
61 4-OCH.sub.3
5-Br HCOCH.sub.3
OCH.sub.2
62 4-OCH.sub.3
5-Br NOCH.sub.3
OCH.sub.2
63 4-OCH.sub.3
5-Br CHCH.sub.3
OCH.sub.2
64 CH.sub.2 C.sub.6 H.sub.5
H HCOCH.sub.3
OCH.sub.2
65 CH.sub.2 C.sub.6 H.sub.5
H NOCH.sub.3
OCH.sub.2
66 CH.sub.2 C.sub.6 H.sub.5
H CHCH.sub.3
OCH.sub.2
__________________________________________________________________________
In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides.
The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.
The novel compounds are particularly useful for controlling the following plant diseases:
Erysiphe graminis in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,
Podosphaera leucotricha in apples,
Uncinula necator in vines,
Puccinia species in cereals,
Rhizoctonia solani in cotton,
Ustilago species in cereals and sugar cane,
Venturia inaeualis (scab) in apples,
Helminthosporium species in cereals,
Septoria nodorum in wheat,
Botrytis cinerea (gray mold) in strawberries and grapes,
Cercospora arachidicola in groundnuts,
Pseudocercosporella herpotrichoides in wheat and barley,
Pyricularia oryzae in rice,
Phytophthora infestans in potatoes and tomatoes,
Fusarium and Verticillium species in various plants,
Plasmopara viticola in grapes,
Alternaria species in fruit and vegetables.
The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi themselves, or the plants, seed, materials or the soil to be protected against fungus attack are treated with a fungicidally effective amount of the active ingredient.
The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose.
The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials (timber), e.g., against Paecilomyces variotii. When the active ingredients are used for treating seed, rates of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are generally sufficient.
The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.
Examples of formulations are given below.
I. A solution of 90 parts by weight of compound no. 2/77 and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very fine drops.
II. A mixture of 20 parts by weight of compound no. 4/65, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and I mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
III. An aqueous dispersion of 20 parts by weight of compound no. 13/8, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
IV. An aqueous dispersion of 20 parts by weight of compound no. 19/2, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.
›CHCH · 2 of 3
V. A hammer-milled mixture of 80 parts by weight of compound no. 19/26, 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.
VI. An intimate mixture of 3 parts by weight of compound no. 2111 and 97 parts by weight of particulate kaolin. The dust contains 3 wt % of the active ingredient.
VII. An intimate mixture of 30 parts by weight of compound no. 2/14, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.
VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 2/24, 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water, which dispersion can be further diluted.
IX. A stable oily dispersion of 20 parts by weight of compound no. 2/77, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.
Methyloxime (B) disclosed in DE 36 23 921, and 2-phenyloxymethylenephenylglyoxylic acid-O-methyloxime (C) disclosed in DE 36 23 921 were used for comparison purposes.
USE EXAMPLE 1
Action on Plasmopara viticola
Leaves of potted vines of the Muller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 8 days in the greenhouse. Then the leaves were infected with a zoospore suspension of Plasmopara viticola. The plants were first placed for 48 hours in a water vapor-saturated chamber at 24° C. and then in a greenhouse for 5 days at from 20° to 30° C. To accelerate and intensify the sporangiophore discharge, the plants were then again placed in the moist chamber for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves. The results show that active ingredients 2/77, 4/65, 13/8, 19/2 and 19/26, applied as 0.006 wt % spray liquors, had a better fungicidal action (85%) than the prior art active ingredients A, B and C (60%).
USE EXAMPLE 2
Action on Pyrenophora teres
Barley seedlings of the "Igri" variety were sprayed to runoff at the 2-leaf stage with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres and placed for 48 hours in a high-humidity climatic cabinet kept at 18° C. The plants were then cultivated for a further 5 days in the greenhouse at 20°-22° C. and a relative humidity of 70%. The extent of fungus spread was then determined.
The results show that active ingredients 2/11, 2/14, 2/24, 2/77, 2/84, 2/456, 2/473, 2/474, 4/8, 4/65, 7/8, 7/66, 13/9, 13/10, 13/65, 13/66, 19/2, 19/26, 19/194, 19/237, 19/238, 19/239, 19/240 and 19/242, applied as 0.05% spray liquors, had a better fungicidal action (95%) than prior art active ingredients B (60%) and C (50%).
The novel compounds are also suitable for effectively combating pests such as insects, arachnids and nematodes. They may be used as pesticides in crop protection and in the hygiene, stores protection and veterinary sector.
Examples of injurious insects belonging to the Lepidoptera order are Agrotis upsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographs gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholita funebrana, Grapholita molests, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includens, Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis.
Examples from the Coleoptera order are Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, melolontha hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorrhynchus sulcatus, Ortiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria.
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Examples from the Diptera order are Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa.
Examples from the Thysanoptera order are Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci.
Examples from the Hymenoptera order are Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testundinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta.
Examples from the Heteroptera order are Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor.
Examples from the nematodes class are root-knot nematodes, e.g., Meloidogyne hapla, Meloidocivne incognita and Meloidogyne javanica, cyst-forming nematodes, e.g., Globodera rostochiensis, Heterodera avenae, Hetrodera glycinae, Heterodera schachtii and Heterodera trifolii, and stem and leaf eelworms, e.g., Belolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.
When the active ingredients are used for combating pests, the concentration of the active ingredients in the finished formulations may vary over a wide range. Generally, they are from 0.0001 to 10, and preferably from 0.001 to 0.1, %.
The active ingredients may also successfully be used in the ultra-low-volume (ULV) method, where it is possible to apply formulations containing more than 95 wt % of active ingredient, or even the active ingredient without additives.
In the open, the amount of active ingredient applied is for example from 0.01 to 10, particularly from 0.01 to 1.0, kg/ha.
Claims
6 · 1 independent · depth 2Classifications
50 codes- A01N37/42
- A01N39/00
- A01N49/00
- A01N53/00
- A01N37/50
- A01N43/40
- A01N39/02
- A01N37/40
- A01N37/38
- A01N43/54
- A01N37/10
- A01N43/74
- A01N39/04
- A01N37/36
- C07D213/79
- C07C251/24
- C07C251/86
- C07C323/57
- C07C251/48
- C07D213/64
- C07D213/70
- C07C323/19
- C07C323/20
- C07D277/70
- C07D239/40
- C07C255/41
- C07C323/56
- C07C229/34
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